(2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester
CAS No.:154161-02-1
Molecular Formula:C₂₂H₃₇NO₄Si
Molecular Weight:407.626
Hs Code.:

Synonyms:(2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester

There total 10 articles about (2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester 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:

: 154161-01-0
[(2S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-ethyl]-carbamic acid benzyl ester

: 154161-02-1
(2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / SnCl₄ / CH₂Cl₂ / 1 h / -78 °C

2: 2,6-lutidine / CH₂Cl₂ / 18 h / 20 °C

3: 81 percent / 4-methylmorpholine N-oxide; OsO₄ / H₂O; acetone; 2-methyl-propan-2-ol / 20 °C

4: sodim periodate; silica gel / CH₂Cl₂; H₂O / 20 °C

5: NaBH₃CN; AcOH / methanol

6: 2.6 g / AcOH / methanol / 1 h / Heating

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; silica gel; tin(IV) chloride; sodium cyanoborohydride; acetic acid; 4-methylmorpholine N-oxide; In methanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1016/S0957-4166(02)00255-0

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 154161-02-1
(2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-lutidine / CH₂Cl₂ / 18 h / 20 °C

2: 81 percent / 4-methylmorpholine N-oxide; OsO₄ / H₂O; acetone; 2-methyl-propan-2-ol / 20 °C

3: sodim periodate; silica gel / CH₂Cl₂; H₂O / 20 °C

4: NaBH₃CN; AcOH / methanol

5: 2.6 g / AcOH / methanol / 1 h / Heating

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; silica gel; sodium cyanoborohydride; acetic acid; 4-methylmorpholine N-oxide; In methanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1016/S0957-4166(02)00255-0

Reference yield:

: 468061-02-1
(1S,2S)-[1-(tert-butyldimethylsilanyloxymethyl)-2-triisopropylsilanyloxypent-4-enyl]carbamic acid benzyl ester

: 154161-02-1
(2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / 4-methylmorpholine N-oxide; OsO₄ / H₂O; acetone; 2-methyl-propan-2-ol / 20 °C

2: sodim periodate; silica gel / CH₂Cl₂; H₂O / 20 °C

3: NaBH₃CN; AcOH / methanol

4: 2.6 g / AcOH / methanol / 1 h / Heating

With sodium periodate; osmium(VIII) oxide; silica gel; sodium cyanoborohydride; acetic acid; 4-methylmorpholine N-oxide; In methanol; dichloromethane; water; acetone; tert-butyl alcohol;
DOI:10.1016/S0957-4166(02)00255-0