(R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol

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Chemical Name:(R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol
CAS No.:252273-59-9
Molecular Formula:C₄₁H₅₂O₉SSi
Molecular Weight:749.01
Hs Code.:

Synonyms:(R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol

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Chemical Property of (R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol

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Technology Process of (R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol

There total 8 articles about (R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-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: 96.0%

: 252273-58-8
trimethyl [5S,6S,7S]-7-(t-butyldiphenylsilyloxy)-5,6-isopropylidenedioxy-4-oxo-7-phenyl-3-phenylsulfonylorthoheptanoate

: 252273-59-9
(R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at -78 ℃; for 1.5h;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 179618-34-9
ethyl (2S,3S,4R)-4-{[(tert-butyl)(dimethyl)silyl]oxy}-2,3-dihydroxy-4-phenylbutanoate

: 252273-59-9
(R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / camphorsulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

2: 95 percent / Et₃N*3HF / acetonitrile / 168 h / 20 °C

3: 97 percent / Ph₃P; ethyl azodicarboxylate / tetrahydrofuran / 1.75 h / 0 - 20 °C

4: 87 percent / K₂CO₃ / CH₂Cl₂; ethanol / 1 h / 20 °C

5: 94 percent / imidazole / dimethylformamide / 96 h / 20 °C

6: 90 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

7: 96 percent / LiAlH₄ / diethyl ether / 1.5 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; ethyl azodicarboxylate; camphor-10-sulfonic acid; potassium carbonate; triethylamine tris(hydrogen fluoride); triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Cyclization / 2: desilylation / 3: Mitsunobu reaction / 4: saponification / 5: silylation / 6: Julia coupling / 7: Reduction;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 187931-99-3
ethyl (4S,5S)-5-[(R)-{[(tert-butyl)(dimethyl)silyl]oxy}(phenyl)methyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

: 252273-59-9
(R)-2-Benzenesulfonyl-1-{(4R,5S)-5-[(S)-(tert-butyl-diphenyl-silanyloxy)-phenyl-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4,4,4-trimethoxy-butan-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / Et₃N*3HF / acetonitrile / 168 h / 20 °C

2: 97 percent / Ph₃P; ethyl azodicarboxylate / tetrahydrofuran / 1.75 h / 0 - 20 °C

3: 87 percent / K₂CO₃ / CH₂Cl₂; ethanol / 1 h / 20 °C

4: 94 percent / imidazole / dimethylformamide / 96 h / 20 °C

5: 90 percent / n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C

6: 96 percent / LiAlH₄ / diethyl ether / 1.5 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; ethyl azodicarboxylate; potassium carbonate; triethylamine tris(hydrogen fluoride); triphenylphosphine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: desilylation / 2: Mitsunobu reaction / 3: saponification / 4: silylation / 5: Julia coupling / 6: Reduction;
DOI:10.1016/S0040-4020(99)00794-2