Crystal Structure of Potential Key Compounds, dl-(1,2,3′,4,5,6′/3,6)-6-Azido-5′-O-t-butyldiphenylsilyl-6-(cyano)hydroxymethyl-3,5-di-C-hydroxymethyl-1,2:3,3′-di-O-isopropylidene-4-O-methoxymethyl-1,2,3,4-cyclohexanetetrol, toward (±)-Tetrodotoxin

Akai, Shoji; Sugita, Naoki; Yoshimura, Juji; Sato, Kenichi

doi:10.2116/analsci.15.503

Cited by 3 publications

(1 citation statement)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…There are few cyclohexane structures in the Cambridge Structural Database (CSD, Version? ; Allen, 2002) with adjacent azide and O substituents, namely CSD refcodes QAPSAB and QAPSEF (Akai, Nakamura et al, 1999;Akai, Sugita et al, 1999), AZUZAW (Busscher et al, 2004) and IXEVAI (Carballido et al, 2004). The azide angular geometries C1-N1-N2 and N1-N2-N3 in (I) fall within the previously observed ranges of 114-119° and 170-174°, respectively.…”

Section: S1 Commentsupporting

confidence: 79%

Non-classical hydrogen bonding involving bound diazides in an inositol derivative

Gainsford¹,

Lensink²,

Falshaw³

et al. 2005

Acta Cryst E

View full text Add to dashboard Cite

Key indicatorsSingle-crystal X-ray study T = 88 K Mean (C-C) = 0.016 Å Disorder in solvent or counterion R factor = 0.053 wR factor = 0.127 Data-to-parameter ratio = 9.3 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e. # 2006 International Union of Crystallography Printed in Great Britain -all rights reserved The inositol derivative 1d-1,2-diazido-1,2-dideoxy-3,4,5,6tetra-O-benzyl-myo-inositol diethyl ether 0.6-solvate, C 34 H 34 N 6 O 4 Á0.6C 4 H 10 O, packs with weak and unusual C-HÁ Á ÁN,O hydrogen bonds and C-HÁ Á Á interactions.Figure 1The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level. The solvent molecule has been omitted. organic papers

show abstract

Section: S1 Commentsupporting

confidence: 79%

Non-classical hydrogen bonding involving bound diazides in an inositol derivative

Gainsford¹,

Lensink²,

Falshaw³

et al. 2005

Acta Cryst E

View full text Add to dashboard Cite

show abstract

Stereocontrolled Total Synthesis of Tetrodotoxin from myo-Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures

Sato

Akai

Yoshimura

2013

Natural Product Communications

Self Cite

View full text Add to dashboard Cite

This report describes the stereocontrolled total synthesis of the multi-functionalized cyclitol derivative, tetrodotoxin, containing eight asymmetric carbons and different types of branched-chains, from myo-inositol and D-glucose using three different methods. The tetrodotoxin derivatives possess a relatively small molecular weight but unique structural and chemical properties. Selection of the appropriate synthetic method may be useful not only for compounds related to TTX (including related derivatives), but also for other highly complex multi-functionalized cyclitols containing branched-chains.

show abstract

Stereocontrolled Total Synthesis of Tetrodotoxin from myo-Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures

Sato

Akai

Yoshimura

2015

Natural Product Communications

Self Cite

View full text Add to dashboard Cite

show abstract

Crystal Structure of Potential Key Compounds, dl-(1,2,3′,4,5,6′/3,6)-6-Azido-5′-O-t-butyldiphenylsilyl-6-(cyano)hydroxymethyl-3,5-di-C-hydroxymethyl-1,2:3,3′-di-O-isopropylidene-4-O-methoxymethyl-1,2,3,4-cyclohexanetetrol, toward (±)-Tetrodotoxin

Cited by 3 publications

References 6 publications

Non-classical hydrogen bonding involving bound diazides in an inositol derivative

Non-classical hydrogen bonding involving bound diazides in an inositol derivative

Stereocontrolled Total Synthesis of Tetrodotoxin from myo-Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures

Stereocontrolled Total Synthesis of Tetrodotoxin from myo-Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures

Contact Info

Product

Resources

About