(2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

• Chemical Name: (2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
• CAS No.: 863297-15-8
• Molecular Formula: C₃₉H₃₆O₅S
• Molecular Weight: 616.778

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

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

Chemical Property:

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

There total 3 articles about (2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-2-phenyl-6-tritylsulfanyl-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%

(2R,4aR,6R,7S,8R,8aS)-2-Phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (863297-14-7) + benzyl bromide (100-39-0) → (2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (863297-15-8)

Guidance literature:

(2R,4aR,6R,7S,8R,8aS)-2-Phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol; With di(n-butyl)tin oxide; cesium fluoride; In toluene; for 3h; Heating;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.tetlet.2005.05.112

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → (2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (863297-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 53 percent / TsOH / dimethylformamide / 6 h / 50 °C

2.1: Bu₂SnO; CsF / toluene / 3 h / Heating

2.2: 91 percent / dimethylformamide / 20 °C

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; cesium fluoride; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2005.05.112

Reference yield:

triphenylmethyl 1-thio-α-D-mannopyranoside (616238-31-4) → (2R,4aR,6R,7S,8R,8aR)-8-Benzyloxy-2-phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (863297-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 53 percent / TsOH / dimethylformamide / 6 h / 50 °C

2.1: Bu₂SnO; CsF / toluene / 3 h / Heating

2.2: 91 percent / dimethylformamide / 20 °C

With di(n-butyl)tin oxide; toluene-4-sulfonic acid; cesium fluoride; In N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2005.05.112

upstream raw materials:

(2R,4aR,6R,7S,8R,8aS)-2-Phenyl-6-tritylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

benzyl bromide

benzaldehyde dimethyl acetal

triphenylmethyl 1-thio-α-D-mannopyranoside

Downstream raw materials:

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

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

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