(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol
• CAS No.: 1105054-60-1
• Molecular Formula: C₂₈H₃₁NO₄
• Molecular Weight: 445.558
• Mol file: 1105054-60-1.mol

Synonyms:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol

Chemical Property of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol

There total 3 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol 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: 98.0%

vinyl magnesium bromide (1826-67-1) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol (1105054-60-1)

Guidance literature:

vinyl magnesium bromide; (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide; In tetrahydrofuran; diethyl ether; at 0 ℃; for 13h;

With ammonium chloride; In tetrahydrofuran; diethyl ether; water; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tet.2009.12.030

Reference yield: 90.0%

vinylmagnesium chloride (3536-96-7) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol (1105054-60-1)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 15h;

DOI:10.1016/j.tet.2008.10.096

Reference yield:

(2R,3S,4S)-2,3,5-tris(benzyloxy)-4-iodopentanal O-(tert-butyldiphenylsilyl) oxime → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-vinylpyrrolidin-1-ol (1105054-60-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 16 h / 20 °C

2: tetrahydrofuran / 0.5 h / 0 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/acs.orglett.1c01248

upstream raw materials:

vinylmagnesium chloride

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

vinyl magnesium bromide

Downstream raw materials:

(2S,3R,4R,5R)-N-butyloxycarbonyl-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidine-2-carbaldehyde

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

C₃₉H₄₅NO₆

C₃₄H₃₇NO₄