1,2-Ethanediol,1-[(3S,4R)-4-hydroxy-3-pyrrolidinyl]-,(1S)-(9CI)

Base Information

• Chemical Name: 1,2-Ethanediol,1-[(3S,4R)-4-hydroxy-3-pyrrolidinyl]-,(1S)-(9CI)
• CAS No.: 362600-09-7
• Molecular Formula: C6H13 N O3
• Molecular Weight: 0
• Mol file: 362600-09-7.mol

Synonyms:1,2-Ethanediol,1-[(3S,4R)-4-hydroxy-3-pyrrolidinyl]-,(1S)-(9CI)

Chemical Property of 1,2-Ethanediol,1-[(3S,4R)-4-hydroxy-3-pyrrolidinyl]-,(1S)-(9CI)

Chemical Property:

• PSA: 72.72000
• LogP: -1.75130

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Ethanediol,1-[(3S,4R)-4-hydroxy-3-pyrrolidinyl]-,(1S)-(9CI)

There total 9 articles about 1,2-Ethanediol,1-[(3S,4R)-4-hydroxy-3-pyrrolidinyl]-,(1S)-(9CI) 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: 71.0%

(3R,4S,5S)-4-Azidomethyl-5-hydroxymethyl-tetrahydro-furan-2,3-diol (1025898-09-2) → (3R,4S)-4-[(1S)-1,2-dihydroxyethyl]-3-hydroxypyrrolidine (362600-09-7,779337-55-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; at 20 ℃; for 24h; under 10343 Torr;

DOI:10.1016/S0008-6215(01)00132-X

Reference yield: 66.0%

3-C-cyano-3-deoxy-α-D-ribo-pentofuranose → (3R,4S)-4-[(1S)-1,2-dihydroxyethyl]-3-hydroxypyrrolidine (362600-09-7,779337-55-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In water; at 20 ℃; for 24h; under 10343 Torr;

DOI:10.1016/S0008-6215(01)00132-X

Reference yield:

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose (103931-45-9) → (3R,4S)-4-[(1S)-1,2-dihydroxyethyl]-3-hydroxypyrrolidine (362600-09-7,779337-55-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran

2.1: BH₃ / tetrahydrofuran

3.1: H₂O₂; NaOH

4.1: pyridine

5.1: dimethylammonium azide

5.2: 82 percent / aq. AcOH

6.1: 71 percent / H₂ / Pd/C / H₂O / 24 h / 20 °C / 10343 Torr

With pyridine; sodium hydroxide; n-butyllithium; dimethyl ammonium azide; borane; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In tetrahydrofuran; water; 1.1: Wittig reaction;

DOI:10.1016/S0008-6215(01)00132-X

upstream raw materials:

(3R,4S,5S)-4-Azidomethyl-5-hydroxymethyl-tetrahydro-furan-2,3-diol

5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

5-O-(tert-butyldimethylsilyl)-3-C-cyano-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose

5-O-(tert-butyldimethylsilyl)-3-C-cyano-1,2-O-isopropylidene-3-O-(phenyloxythiocarbonyl)-α-D-xylo-pentofuranose

Downstream raw materials:

N-(pyren-1-ylmethyl)-(3R,4R)-4-[(4,4'-dimethoxytriphenylmethoxy)methyl]pyrrolidin-3-ol