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

Base Information

Chemical Name:(2R,4aR,6S,7S,8S,8aS)-8-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
CAS No.:881895-19-8
Molecular Formula:C₂₀H₂₁N₃O₄S
Molecular Weight:399.47
Hs Code.:

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

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

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

There total 1 articles about (2R,4aR,6S,7S,8S,8aS)-8-Azido-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-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: 91.0%

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

: 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

Guidance literature:: With sodium azide; ammonium chloride; In dimethyl sulfoxide; at 80 ℃; for 6h;
DOI:10.1021/ol0601996

Reference yield: 86.0%

: 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

: 100-39-0
benzyl bromide

: 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

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 30h;
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

: 881895-22-3
(3S,4R,5S,6R)-4-Azido-3-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2,5-diol

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 92 percent / N-bromosuccinimide / acetone; H₂O / 20 °C

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