(2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 154161-04-3
• Molecular Formula: C₂₂H₃₅NO₄Si
• Molecular Weight: 405.61
• Mol file: 154161-04-3.mol

Synonyms:(2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property of (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester

There total 11 articles about (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester (154161-04-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: OsO₄, NMO / acetone; H₂O / Ambient temperature

3: NaIO₄, silica gel / CH₂Cl₂ / Ambient temperature

4: NaBH₃CN / acetic acid; methanol / Ambient temperature

5: acetic acid; methanol / 1 h / Heating

6: NaOCl, TEMPO, KBr, NaHCO₃ / ethyl acetate; toluene; H₂O / 0 °C

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; silica gel; sodium cyanoborohydride; sodium hydrogencarbonate; potassium bromide; In methanol; dichloromethane; water; acetic acid; ethyl acetate; acetone; toluene;

DOI:10.1016/S0040-4039(00)61611-8

Reference yield:

(2S,3S)-2-(hydroxymethyl)-3-triisopropylsilanyloxypyrrolidine-1-carboxylic acid benzyl ester (154161-02-1) → (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester (154161-04-3)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide; In water; ethyl acetate; toluene; at 0 ℃;

DOI:10.1016/S0040-4039(00)61611-8

Reference yield:

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → (2R,3S)-2-Formyl-3-triisopropylsilanyloxy-pyrrolidine-1-carboxylic acid benzyl ester (154161-04-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / imidazole / dimethylformamide

2: 95 percent / NaBH₄ / methanol / 50 °C

3: 95 percent / TEMPO-NaOCl

4: 60 percent / SnCl₄ / CH₂Cl₂ / -78 °C

5: 2,6-lutidine / CH₂Cl₂ / 0 °C

6: OsO₄, NMO / acetone; H₂O / Ambient temperature

7: NaIO₄, silica gel / CH₂Cl₂ / Ambient temperature

8: NaBH₃CN / acetic acid; methanol / Ambient temperature

9: acetic acid; methanol / 1 h / Heating

10: NaOCl, TEMPO, KBr, NaHCO₃ / ethyl acetate; toluene; H₂O / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; silica gel; tin(IV) chloride; sodium cyanoborohydride; sodium hydrogencarbonate; potassium bromide; In methanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/S0040-4039(00)61611-8

upstream raw materials:

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

N-benzyloxycarbonyl-L-serine methyl ester

triisopropylsilyl trifluoromethanesulfonate

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

Downstream raw materials:

(2R,3S)-3-triisopropylsilanyloxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

(2R,3S)-N-(benzyloxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Refernces