Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester

Base Information

• Chemical Name: Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester
• CAS No.: 203389-77-9
• Molecular Formula: C₃₂H₃₃O₇P
• Molecular Weight: 560.584
• Mol file: 203389-77-9.mol

Synonyms:Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester

Chemical Property of Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester

There total 11 articles about Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-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: 82.0%

Phosphoric acid dibenzyl ester (2R,3R)-2,3-bis-benzyloxy-4-hydroxy-butyl ester (203389-76-8) → Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester (203389-77-9)

Guidance literature:

With 3 A molecular sieve; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/j.tetlet.2006.11.091

Reference yield:

(2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol (113350-84-8) → Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester (203389-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / NaH / tetrahydrofuran

2: 81 percent / tetrazole; mCPBA / CH₂Cl₂

3: 87 percent / tetrabutylammonium fluoride / tetrahydrofuran

4: 82 percent / PCC; 3 Angstroem molecular sieves / CH₂Cl₂

With 1H-tetrazole; 3 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2006.11.091

Reference yield:

benzyl bromide (100-39-0) → Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-butyl ester (203389-77-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / thallous ethoxide / acetonitrile / 1.) 55 deg C, 48 h, 2.) room temp., 12 h

2: 83.3 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

3: 40 percent / CCl₄; pyridine / 12 h / Ambient temperature

4: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -10 deg C, 10 min, 2.) CH₂Cl₂, -10 deg C, 5 min

With lithium aluminium tetrahydride; oxalyl dichloride; thallium (I) ethoxide; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; tetrachloromethane; acetonitrile;

DOI:10.1021/jo971933p

upstream raw materials:

Phosphoric acid dibenzyl ester (2R,3R)-2,3-bis-benzyloxy-4-hydroxy-butyl ester

phosphoric acid dibenzyl ester 2,3-bis-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-butyl ester

(2R,3R)-(-)-2,3-bis(phenylmethoxy)-1,4-butanediol

(2R,3R)-2,3-bis(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)butan-1-ol

Downstream raw materials:

Phosphoric acid dibenzyl ester (2R,3S)-2,3-bis-benzyloxy-4-oxo-pentyl ester

phosphoric acid dibenzyl ester 2,3-bis-benzyloxy-5,5,5-trifluoro-4-hydroxy-pentyl ester

Phosphoric acid dibenzyl ester (2R,3R)-2,3-bis-benzyloxy-4-hydroxy-pentyl ester