(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:231618-90-9
Molecular Formula:C₃₃H₄₁NO₈S
Molecular Weight:611.756
Hs Code.:

Synonyms:(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 17 articles about (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl 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: 100.0%

: 124-63-0
methanesulfonyl chloride

: 231618-88-5
(2R,3R,4R,5R)-N-butyloxycarbonyl-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>-2-(hydroxymethyl)pyrrolidine

: 231618-90-9
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2h;

Reference yield:

: 765308-79-0
1-(tert-butyl-dimethyl-sylanyloxy)-2-deoxy-2-azido-3,4,6-tri-O-benzyl-5-oxo-D-mannitol

: 231618-90-9
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: hydrogen / Pd-C / tetrahydrofuran; pyridine / 4 h / 760 Torr

2: 7 mg / NaBH₃CN; p-TsOH / methanol / 20 °C

3: 97 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

4: 83 percent / Et₃N / CH₂Cl₂ / 20 °C

5: Et₃N / CH₂Cl₂ / 2 h / 0 °C

With tetrabutyl ammonium fluoride; hydrogen; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane;
DOI:10.1021/jo049355h

Reference yield:

: 765308-77-8
2-deoxy-2-azido-3,4,6-tri-O-benzyl-D-mannitol

: 231618-90-9
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 71 percent / pyridine / 0 °C

2: 91 percent / Dess-Martin reagent / CH₂Cl₂ / 0 - 20 °C

3: hydrogen / Pd-C / tetrahydrofuran; pyridine / 4 h / 760 Torr

4: 7 mg / NaBH₃CN; p-TsOH / methanol / 20 °C

5: 97 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

6: 83 percent / Et₃N / CH₂Cl₂ / 20 °C

7: Et₃N / CH₂Cl₂ / 2 h / 0 °C

With pyridine; tetrabutyl ammonium fluoride; hydrogen; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane;
DOI:10.1021/jo049355h