(2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Base Information

Chemical Name:(2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
CAS No.:634597-88-9
Molecular Formula:C₃₅H₃₈O₅SSi
Molecular Weight:598.835
Hs Code.:

Synonyms:(2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Chemical Property of (2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

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Technology Process of (2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

There total 1 articles about (2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-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: 71.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 159407-19-9
phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 634597-88-9
(2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Guidance literature:: phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With di(n-butyl)tin oxide; In methanol; for 1h; Heating;

tert-butylchlorodiphenylsilane; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; for 16h;
DOI:10.1002/anie.200351950

Reference yield: 95.0%

: 108-24-7
acetic anhydride

: 634597-88-9
(2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 634597-89-0
Acetic acid (2R,4aR,6R,7S,8S,8aR)-8-(tert-butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

Guidance literature:: With pyridine; dmap; for 2h;
DOI:10.1002/anie.200351950

Reference yield:

: 634597-88-9
(2R,4aR,6R,7S,8R,8aR)-8-(tert-Butyl-diphenyl-silanyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 4-oxo-pentanoic acid 5-acetoxy-4-(tert-butyl-diphenyl-silanyloxy)-2-(9H-fluoren-9-ylmethoxycarbonyloxymethyl)-6-hydroxy-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / N,N-dimethylpyridin-4-amine; pyridine / 2 h

2: 92 percent / BF₃*OEt₂; C₂H₅SH / CH₂Cl₂

3: 85 percent / pyridine; N,N-dimethylpyridin-4-amine / acetonitrile / 1 h

4: 85 percent / N,N-dimethylpyridin-4-amine; dicyclohexylcarbodiimide / 1.5 h

5: 90 percent / N-bromosuccinimide; H₂O / acetone / 2 h / -20 °C

With pyridine; dmap; N-Bromosuccinimide; boron trifluoride diethyl etherate; water; dicyclohexyl-carbodiimide; ethanethiol; In dichloromethane; acetone; acetonitrile;
DOI:10.1002/anie.200351950