(1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol

Base Information

Chemical Name:(1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol
CAS No.:174647-71-3
Molecular Formula:C₃₃H₃₈O₆SSi
Molecular Weight:590.813
Hs Code.:

Synonyms:(1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol

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Chemical Property of (1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol

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Technology Process of (1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol

There total 13 articles about (1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol 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: 72.0%

: 98-59-9
p-toluenesulfonyl chloride

: 174757-48-3
(1R,2S,3R)-1-(t-butyldiphenylsilyloxy)-1-phenylbutane-2,3,4-triol

: 174647-71-3
(1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -20 ℃;
DOI:10.1016/0040-4039(95)02125-6

Reference yield:

: 174647-67-7
(1R,2R)-1-(t-butyldiphenylsilyloxy)-1-phenylbut-3-en-2-ol

: 174647-71-3
(1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / N-methylmorpholine N-oxide monohydrate, OsO₄ / acetone; H₂O; butan-1-ol / 5 h

2: CH₂Cl₂ / 0.17 h / Ambient temperature

3: 100 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, 4A molecular sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 72 percent / L-selectride / tetrahydrofuran / -100 °C

5: 85 percent / aq. AcOH / 3 h / Heating

6: 72 percent / 4-dimethylaminopyridine / CH₂Cl₂ / -20 °C

With dmap; osmium(VIII) oxide; tetrapropylammonium perruthennate; 4 A molecular sieve; L-Selectride; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; acetone; butan-1-ol;
DOI:10.1016/0040-4020(96)00918-0

Reference yield:

: 174647-66-6
(R)-4-(t-butyldiphenylsilyloxy)-4-phenylbut-1-en-3-one

: 174647-71-3
(1R,2S,3S)-1-(t-butyldiphenylsilyloxy)-1-phenyl-4-(p-toluenesulfonyloxy)butane-2,3-diol

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / NaBH₄, CeCl₃*7H₂O / methanol / 1 h / -78 °C

2: 90 percent / N-methylmorpholine N-oxide monohydrate, OsO₄ / acetone; H₂O; butan-1-ol / 5 h

3: CH₂Cl₂ / 0.17 h / Ambient temperature

4: 100 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate, 4A molecular sieves / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 72 percent / L-selectride / tetrahydrofuran / -100 °C

6: 85 percent / aq. AcOH / 3 h / Heating

7: 72 percent / 4-dimethylaminopyridine / CH₂Cl₂ / -20 °C

With dmap; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; tetrapropylammonium perruthennate; 4 A molecular sieve; L-Selectride; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; butan-1-ol;
DOI:10.1016/0040-4020(96)00918-0