(2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol
• CAS No.: 110403-98-0
• Molecular Formula: C₃₃H₃₈N₆O₉S
• Molecular Weight: 694.766

Synonyms:

Chemical Property of (2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol

There total 2 articles about (2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-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:

phenylthiotrimethylsilane (4551-15-9) → (2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol (110403-98-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ZnI₂ / 1,2-dichloro-ethane / Ambient temperature

2: aq.AcOH

With acetic acid; zinc(II) iodide; In 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)96231-2

Reference yield:

C42H62N6O9SSi3 → (2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol (110403-98-0)

Guidance literature:

With acetic acid;

DOI:10.1016/S0040-4039(00)96231-2

Reference yield: 76.0%

(2R,3S,4S,5R,6R)-5-Azido-2-azidomethyl-6-[(2R,3R,4S,5R)-4-benzyloxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4-diol (110403-98-0) + 2,2-dimethoxy-propane (77-76-9) → phenyl 3-O-benzyl-4-O-(2,6-diazido-2,6-dideoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-1-thio-D-glucopyranoside (110424-95-8)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1016/S0040-4039(00)96231-2

upstream raw materials:

phenylthiotrimethylsilane

Downstream raw materials:

phenyl 3-O-benzyl-4-O-(2,6-diazido-2,6-dideoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-1-thio-D-glucopyranoside

phenyl 3-O-benzyl-4-O-(2,6-diazido-2,6-dideoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-1-thio-β-D-glucopyranoside

phenyl 3-O-benzyl-4-O-(2,6-diazido-2,6-dideoxy-3,4-O-isopropylidene-α-D-allopyranosyl)-2-O-(p-methoxybenzyl)-1-thio-α-D-glucopyranoside

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