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

Base Information

Chemical Name:(2R,3S,4R,5S,6S)-4-Azido-5-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol
CAS No.:881895-21-2
Molecular Formula:C₂₇H₂₉N₃O₄S
Molecular Weight:491.611
Hs Code.:

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

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

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

There total 3 articles about (2R,3S,4R,5S,6S)-4-Azido-5-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol 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: 95.0%

: 881895-20-1
(2R,4aR,6S,7S,8R,8aS)-8-Azido-7-benzyloxy-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 881895-21-2
(2R,3S,4R,5S,6S)-4-Azido-5-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: With hydrochloric acid diethyl ether; sodium cyanoborohydride; In tetrahydrofuran; at 20 ℃; for 0.166667h;
DOI:10.1021/ol0601996

Reference yield:

: 872593-83-4
p-tolyl 2,3-anhydro-4,6-O-benzylidene-1-thio-β-D-mannopyranoside

: 881895-21-2
(2R,3S,4R,5S,6S)-4-Azido-5-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

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

2: 86 percent / sodium hydride / dimethylformamide / 30 h / 20 °C

3: 95 percent / sodium cyanoborohydride; HCl*Et₂O / tetrahydrofuran / 0.17 h / 20 °C

With sodium azide; ammonium chloride; hydrochloric acid diethyl ether; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/ol0601996

Reference yield:

: 881895-19-8
(2R,4aR,6S,7S,8S,8aS)-8-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 881895-21-2
(2R,3S,4R,5S,6S)-4-Azido-5-benzyloxy-2-benzyloxymethyl-6-p-tolylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / sodium hydride / dimethylformamide / 30 h / 20 °C

2: 95 percent / sodium cyanoborohydride; HCl*Et₂O / tetrahydrofuran / 0.17 h / 20 °C

With hydrochloric acid diethyl ether; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/ol0601996