(2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:868759-81-3
Molecular Formula:C₂₃H₂₅N₃O₄S
Molecular Weight:439.535
Hs Code.:

Synonyms:(2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 4 articles about (2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 58.0%

: 868759-80-2
Methanesulfonic acid (2R,4aR,6S,7R,8S,8aR)-6-allylsulfanyl-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: 868759-81-3
(2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 70 ℃; for 8h;
DOI:10.1055/s-2005-872244

Reference yield:

: (2S,3R,4S,5S,6R)-2-Allylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

: 868759-81-3
(2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 67 percent / p-TsOH / dimethylformamide / 2 h / 50 °C

2.1: BuSnO; CsF / toluene / 3 h / Heating

2.2: 86 percent / dimethylformamide / 12 h

3.1: pyridine / 2 h

4.1: 58 percent / NaN₃ / dimethylformamide / 8 h / 70 °C

With pyridine; sodium azide; BuSnO; toluene-4-sulfonic acid; cesium fluoride; In N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-2005-872244

Reference yield:

: 868759-78-8
(2R,4aR,6S,7R,8R,8aS)-6-Allylsulfanyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

: 868759-81-3
(2R,4aR,6S,7S,8S,8aR)-7-Allylsulfanyl-6-azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: Multi-step reaction with 3 steps

1.1: BuSnO; CsF / toluene / 3 h / Heating

1.2: 86 percent / dimethylformamide / 12 h

2.1: pyridine / 2 h

3.1: 58 percent / NaN₃ / dimethylformamide / 8 h / 70 °C

With pyridine; sodium azide; BuSnO; cesium fluoride; In N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-2005-872244