Preparation of 6-Acetamido-1,2,3,4-tetra-O-acetyl-6-deoxy-L-idothiapyranose<sup>1</sup>

Goodman, Leon; Christensen, James E.

doi:10.1021/jo01030a029

Cited by 13 publications

(3 citation statements)

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“…The selective reduction of S-and O-benzyl groups by sodium was accomplished in the synthesis of 6-acetamidol,2,3,4-tetra-0-acetyl-6-deoxy-L-idothiapyranose in the presence of an Q-isopropylidene group. 148 The removal of S-and O-benzyl and O-benzylidene groups was reported in the synthesis of /3-amino mercaptans derived from D-altrose,149 methyl 3-thio-a-D-arabinofuranoside,150 methyl 2-deoxy-3-mercapto-and 2mercapto-3-deoxy-a-D-altropyranosides,151 and /3-dglucopyranose derivatives. 152 The O-tosyl group was selectively cleaved by sodium from O-isopropylideneprotected a-D-xylo-and a-D-glucofuranose derivatives.…”

Section: Scope Of Applicationsmentioning

confidence: 99%

Sodium-liquid ammonia reduction in peptide chemistry

Schön¹

1984

Chem. Rev.

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Section: Scope Of Applicationsmentioning

confidence: 99%

Sodium-liquid ammonia reduction in peptide chemistry

Schön¹

1984

Chem. Rev.

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“…The N-acetyl derivatives of (58), (62), and (68) all contain amido groupings with hindered rotation [lsal. The N,N-diacetyl derivative of (58) is particularly interesting. It contains two amido groupings with hindered rotation in the same molecule, so that this compound can exist in four isomeric forms, the struc-remains hindered.…”

Section: Hohcg/"~ G O H Homentioning

confidence: 99%

“…The so-called primary cleavage B in this case leads to the methoxypyridinium ion with MN 110. The precise fragmentation routes for the peracetylated bicyclic idosan derivatives (58),(62), and (68) havealso beendetermined [46cl.…”

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Carbohydrates Containing Nitrogen or Sulfur in the “Hemiacetal” Ring

Paulsen

1966

Angew. Chem. Int. Ed. Engl.

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P: measured degree of polarization; PO: limiting degree of polarization for the frozen solution; T: lifetime of the excited state; 9 : viscosity of the solvent at the temperature T; V : (effective) molecular volume.In 5-amino-5-deoxy-and 5-thioaldoses, a 6-membered hemiace tal ring can be formed by incorporation of a nitrogen or sulfur atom into the ring instead of the oxygen present in pyranoses. In the case of 5-(N-acylamido)-5-deoxyaldoses, the nucleophilic strength of the amide grouping is lowered, with the result that ring closure occurs only when sterically favored, or when a side reaction with formation of furanose is not possible. On the other hand, 5-amino-5-deoxyaldoses containing a free amino group readily form 6-membered "hemiacetal" rings. The resulting piperidinoses possess properties that are unusual in sugars, since they contain the 2-hydroxypiperidine ring system. Piperidinoses are stable to alkalis and labile to acids; they rearrange in the presence of acids to give Amadori compounds, or lose three molecules of water to give derivatives of p-hydroxypyridines. Owing to the high reactivity of the mercapto group, 5-thioaldoses form only sugars with rings containing sulfur, the behavior of which resembles that of the oxygen analogues. 4-Amino-4-deoxy-and 4-thioaldoses can form 5-membered rings containing nitrogen and sulfur.

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