(2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl ester

Base Information

• Chemical Name: (2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl ester
• CAS No.: 91876-53-8
• Molecular Formula: C₃₁H₄₂N₂O₉Si
• Molecular Weight: 614.768
• Mol file: 91876-53-8.mol

Synonyms:

Chemical Property of (2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl ester

There total 5 articles about (2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl 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: 87.0%

benzoyl chloride (98-88-4) + (2R,3R,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-3,4-dihydroxy-pyrrolidine-1-carboxylic acid ethyl ester (91876-49-2,91876-59-4,93091-08-8) → (2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl ester (91876-53-8)

Guidance literature:

DOI:10.1016/S0040-4039(01)90037-1

Reference yield:

(E)-2,4-pentadien-1-ol (4949-20-6,52192-01-5) → (2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl ester (91876-53-8)

Guidance literature:

Multi-step reaction with 5 steps

2: LDA / -45 °C

3: 88 percent

4: 79 percent / OsO₄, N-methylmorpholin-N-oxide

5: 87 percent

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; lithium diisopropyl amide;

DOI:10.1016/S0040-4039(01)90037-1

Reference yield:

3-Hydroxymethyl-3,6-dihydro-pyridazine-1,2-dicarboxylic acid diethyl ester (91876-42-5) → (2R,3R,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-pyrrolidine-1-carboxylic acid ethyl ester (91876-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1: LDA / -45 °C

2: 88 percent

3: 79 percent / OsO₄, N-methylmorpholin-N-oxide

4: 87 percent

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; lithium diisopropyl amide;

DOI:10.1016/S0040-4039(01)90037-1

upstream raw materials:

benzoyl chloride

(2R,3R,4S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-5-ethoxycarbonylamino-3,4-dihydroxy-pyrrolidine-1-carboxylic acid ethyl ester

(E)-2,4-pentadien-1-ol

3-Hydroxymethyl-3,6-dihydro-pyridazine-1,2-dicarboxylic acid diethyl ester

Downstream raw materials:

(2S,3S,4S,5R)-3,4-Bis-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-methoxy-pyrrolidine-1-carboxylic acid ethyl ester