(1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

Base Information

Chemical Name:(1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol
CAS No.:864862-07-7
Molecular Formula:C₃₃H₃₇N₉O₆
Molecular Weight:655.713
Hs Code.:

Synonyms:(1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

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Chemical Property of (1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

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Technology Process of (1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

There total 4 articles about (1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 29.0%

: 863908-09-2
(1S,3S,4S,6S)-4,6-diazidocyclohexane-1,3-diol

: 236115-70-1
6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside

: 864862-07-7
(1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

Guidance literature:: With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 0 ℃; for 3h;
DOI:10.1039/b505865a

Reference yield:

: 16063-09-5
(1S,3S,5R,7R)-4,8-dioxa-tricyclo[5.1.0.0]octane

: 864862-07-7
(1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

Guidance literature:: Multi-step reaction with 3 steps

1: (R,R)-(salen)Cr(III)Cl complex / diethyl ether / 96 h

2: 97 percent / TFA / methanol / 0.58 h

3: 29 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂; diethyl ether / 3 h / 0 °C

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; trifluoroacetic acid; (R,R)-(salen)Cr(III)Cl; In methanol; diethyl ether; dichloromethane;
DOI:10.1039/b505865a

Reference yield:

: 1165952-92-0
cyclohexa-1,4-diene

: 864862-07-7
(1S,3S,4S,6S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexane-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: H₂O₂; pyridine / MeReO₃ / CH₂Cl₂

1.2: 75 percent / MnO₂ / CH₂Cl₂

2.1: (R,R)-(salen)Cr(III)Cl complex / diethyl ether / 96 h

3.1: 97 percent / TFA / methanol / 0.58 h

4.1: 29 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; AgOTf / CH₂Cl₂; diethyl ether / 3 h / 0 °C

With pyridine; N-iodo-succinimide; 4 A molecular sieve; dihydrogen peroxide; silver trifluoromethanesulfonate; trifluoroacetic acid; (R,R)-(salen)Cr(III)Cl; methyltrioxorhenium(VII); In methanol; diethyl ether; dichloromethane;
DOI:10.1039/b505865a