tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane
• CAS No.: 213536-10-8
• Molecular Formula: C₂₅H₄₀O₅SSi
• Molecular Weight: 480.741
• Mol file: 213536-10-8.mol

Synonyms:tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane

Chemical Property of tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane

There total 3 articles about tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane 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: 92.0%

diphenyldisulfane (882-33-7) + (1R,2'S,3'S,3R,4S,5R)-1-hydroxymethyl-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohexane-1,3,4,5-tetraol (213536-07-3) → tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane (213536-10-8)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(98)01239-8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane (213536-10-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / imidazole / CH₂Cl₂

2: 97 percent / DIBAL / tetrahydrofuran / 0 °C

3: 92 percent / n-Bu₃P / tetrahydrofuran / Ambient temperature

With 1H-imidazole; tributylphosphine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(98)01239-8

Reference yield:

(2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate (213536-05-1) → tert-Butyl-((2S,3S,4aS,5R,8aR)-2,3-dimethoxy-2,3-dimethyl-7-phenylsulfanylmethyl-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxin-5-yloxy)-dimethyl-silane (213536-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / DIBAL / tetrahydrofuran / 0 °C

2: 92 percent / n-Bu₃P / tetrahydrofuran / Ambient temperature

With tributylphosphine; diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01239-8

upstream raw materials:

diphenyldisulfane

(1R,2'S,3'S,3R,4S,5R)-1-hydroxymethyl-3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)cyclohexane-1,3,4,5-tetraol

tert-butyldimethylsilyl chloride

(2'S,3'S)-methyl 3-O-tert-butyl(dimethyl)silyl-4-O,5-O-(2',3'-dimethoxybutane-2',3'-diyl)quinate

Downstream raw materials:

((1aR,2S,2aS,4S,5S,6aR,7aS)-7a-Benzenesulfonylmethyl-4,5-dimethoxy-4,5-dimethyl-octahydro-1,3,6-trioxa-cyclopropa[b]naphthalen-2-yloxy)-tert-butyl-dimethyl-silane

shikimic acid

{(1R,2R,4S,5S,7S,8R,9S)-13-[1-Benzenesulfonyl-meth-(E)-ylidene]-4,5-dimethoxy-4,5-dimethyl-3,6,10,12-tetraoxa-tricyclo[7.3.1.0^2,7]tridec-8-yloxy}-tert-butyl-dimethyl-silane

(2S,3S,4aR,5R,7S,8R,8aS)-6-[1-Benzenesulfonyl-meth-(E)-ylidene]-8-(tert-butyl-dimethyl-silanyloxy)-2,3-dimethoxy-2,3-dimethyl-octahydro-benzo[1,4]dioxine-5,7-diol