(S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

Base Information

Chemical Name:(S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol
CAS No.:307532-34-9
Molecular Formula:C₃₅H₄₂O₆SSi
Molecular Weight:618.866
Hs Code.:

Synonyms:(S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

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Chemical Property of (S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

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Technology Process of (S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

There total 5 articles about (S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol 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: 87.0%

: 98-59-9
p-toluenesulfonyl chloride

: 261959-92-6
(S)-1-O-benzyl-3-O-(tert-butyldiphenylsilyl)-2-O-(2-hydroxyethyl)glycerol

: 307532-34-9
(S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

Guidance literature:: With pyridine;
DOI:10.1081/SCC-120004151

Reference yield:

: 56552-80-8
(R)-3-benzyloxy-1,2-propanediol

: 307532-34-9
(S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / imidazole / dimethylformamide

2.1: NaH / tetrahydrofuran / 45 h

2.2: 93 percent / tetrahydrofuran / 4 h

3.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 24 h / 20 °C

3.2: Pb(OAc)4 / tetrahydrofuran / 1 h

3.3: 81 percent / NaBH₄; NaOH / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

4.1: 87 percent / pyridine / 16 h / 0 - 5 °C

With pyridine; 1H-imidazole; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Substitution / 2.1: Etherification / 2.2: Substitution / 3.1: Dihydroxylation / 3.2: Elimination / 3.3: Reduction / 4.1: Tosylation;
DOI:10.1021/jo000766h

Reference yield:

: 99298-07-4
1-O-(tert-butyldiphenylsilyl)-3-O-benzyl-sn-glycerol

: 307532-34-9
(S)-1-O-benzyl-3-O-tert-butyldiphenylsilyl-2-O-[2-(p-toluenesulfonyloxy)ethyl]glycerol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 45 h

1.2: 93 percent / tetrahydrofuran / 4 h

2.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 24 h / 20 °C

2.2: Pb(OAc)4 / tetrahydrofuran / 1 h

2.3: 81 percent / NaBH₄; NaOH / tetrahydrofuran; H₂O / 2 h / 0 - 20 °C

3.1: 87 percent / pyridine / 16 h / 0 - 5 °C

With pyridine; osmium(VIII) oxide; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; tert-butyl alcohol; 1.1: Etherification / 1.2: Substitution / 2.1: Dihydroxylation / 2.2: Elimination / 2.3: Reduction / 3.1: Tosylation;
DOI:10.1021/jo000766h