(2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran
CAS No.:881895-14-3
Molecular Formula:C₂₇H₂₈N₆O₃S
Molecular Weight:516.624
Hs Code.:

Synonyms:(2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran

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Chemical Property of (2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran

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Technology Process of (2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran

There total 6 articles about (2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran 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: 81.0%

: 881895-13-2
p-methylphenyl 2,3-dideoxy-2,3-diazido-1-thio-β-D-mannopyranoside

: 100-39-0
benzyl bromide

: 881895-14-3
(2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/ol0601996

Reference yield: 71.0%

: 881895-13-2
p-methylphenyl 2,3-dideoxy-2,3-diazido-1-thio-β-D-mannopyranoside

: 100-39-0
benzyl bromide

: 881895-14-3
(2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran

: 905704-12-3
(4,5-diazido-3-benzyloxy-6-p-tolylsulfanyl-tetrahydro-pyran-2-yl)-methanol

: 4,5-diazido-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: p-methylphenyl 2,3-dideoxy-2,3-diazido-1-thio-β-D-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at -15 ℃; for 0.0833333h;

benzyl bromide; In N,N-dimethyl-formamide; at -15 - 20 ℃; for 0.5h;
DOI:10.1055/s-2006-939681

Reference yield:

: 872593-76-5
p-tolyl 2,3-anhydro-4,6-O-benzylidene-1-thio-β-D-allopyranoside

: 881895-14-3
(2S,3S,4R,5S,6R)-3,4-Diazido-5-benzyloxy-6-benzyloxymethyl-2-p-tolylsulfanyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / sodium azide; ammonium chloride / dimethylsulfoxide / 6 h / 80 °C

2: pyridine / CH₂Cl₂

3: 9.12 g / sodium azide / dimethylformamide / 0.5 h / 20 °C

4: 96 percent / iodine; methanol / 1 h / Heating

5: 81 percent / sodium hydride / dimethylformamide / 4 h / 20 °C

With pyridine; methanol; sodium azide; ammonium chloride; iodine; sodium hydride; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ol0601996