[1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane

Base Information

Chemical Name:[1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane
CAS No.:171411-70-4
Molecular Formula:C₃₀H₃₆O₆SSi
Molecular Weight:552.764
Hs Code.:

Synonyms:[1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane

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Chemical Property of [1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane

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Technology Process of [1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane

There total 4 articles about [1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane 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: 74.0%

: 256343-23-4
(3aS,5S,7S,7aS)-7-Benzenesulfonyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furo[3,2-b]pyran-3-one

: 171411-70-4
[1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(99)00834-0

Reference yield:

: 171411-65-7
[2S,4S]-2-(tert-butyldiphenylsilyloxymethyl)-4-phenylsulfonyl-3,4-dihydro-2H-pyran

: 171411-70-4
[1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 4 steps

1.1: m-CPBA / diethyl ether; H₂O / 16 h

1.2: 471 mg / (n-Bu)3P / CH₂Cl₂ / 0.5 h / 25 °C

2.1: 86 percent / NaOH; Aliquat 336 / CH₂Cl₂; H₂O / 0.25 h / 25 °C

3.1: AgOTf; 4A molecular sieves; DBU / CH₂Cl₂ / 25 °C

3.2: 79 percent / ozone; triphenylphosphine / CH₂Cl₂ / -78 - 25 °C

4.1: 74 percent / NaBH₄ / methanol / 1 h / 0 °C

With sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; silver trifluoromethanesulfonate; Aliquat 336; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; dichloromethane; water; 1.1: Oxidation / 1.2: Substitution / 2.1: Etherification / 3.1: Cyclization / 3.2: Oxidation / 4.1: Reduction;
DOI:10.1016/S0040-4020(99)00834-0

Reference yield:

: 256343-19-8
[2S,3R,4S,6S]-6-(tert-butyldiphenylsilyloxymethyl)-3-(3-phenyl-2-propenyloxy)-4-phenylsulfonyl-2-(2-thiopyridyl)tetrahydro-2H-pyran

: 171411-70-4
[1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 2 steps

1.1: AgOTf; 4A molecular sieves; DBU / CH₂Cl₂ / 25 °C

1.2: 79 percent / ozone; triphenylphosphine / CH₂Cl₂ / -78 - 25 °C

2.1: 74 percent / NaBH₄ / methanol / 1 h / 0 °C

With sodium tetrahydroborate; 4 A molecular sieve; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; 1.1: Cyclization / 1.2: Oxidation / 2.1: Reduction;
DOI:10.1016/S0040-4020(99)00834-0