(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone

Base Information

• Chemical Name: (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone
• CAS No.: 149818-33-7
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• Mol file: 149818-33-7.mol

Synonyms:(+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone

Chemical Property of (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone

There total 4 articles about (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone 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: 95.0%

(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one (115857-84-6) → (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone (149818-33-7)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; Heating;

DOI:10.1021/jo991984h

Reference yield:

1-(4-methoxyphenyl)-3-(phenylmethoxy)-4-(1,4-dioxaspiro<4.5>dec-2-yl)azetidin-2-one (141268-44-2) → (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone (149818-33-7)

Guidance literature:

With trifluoroacetic acid; In water; Yield given; Ambient temperature;

DOI:10.1021/jo00069a048

Reference yield:

[(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine (141781-23-9) → (+)-(3R,4S)-cis-3-benzyloxy-4-[(S)-1',2'-dihydroxyethyl]-1-(p-methoxyphenyl)-2-azetidinone (149818-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) TiCl₄, TEA / 1.) CH₂Cl₂, -78 deg C, 30 min., 2.) CH₂Cl₂, 0 deg C, 5 h

2: TFA / H₂O / Ambient temperature

With TEA; titanium tetrachloride; trifluoroacetic acid; In water;

DOI:10.1021/jo00069a048

upstream raw materials:

1-(4-methoxyphenyl)-3-(phenylmethoxy)-4-(1,4-dioxaspiro<4.5>dec-2-yl)azetidin-2-one

(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-1-(4-methoxyphenyl)azetidin-2-one

S-(2-Pyridyl) 2-(phenylmethoxy)ethanethioate

[(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-meth-(E)-ylidene]-(4-methoxy-phenyl)-amine

Downstream raw materials:

(+)-(3R,4R)-1-(p-anisyl)-3-benzyloxy-4-formyl-2-azetidinone

(+)-(2S)-[(2R,3R)-3-benzyloxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl][tert-butyl(dimethyl)silyloxy]acetonitrile

(+)-(2S,3R,4R)-4-benzyloxy-2-[tert-butyl(dimethyl)silyloxy]-5-hydroxy-3-[(4-methoxyphenyl)amino]pentanenitrile

tert-butyl (-)-(1R,2R)-2-benzyloxy-1-[(S)-[tert-butyl(dimethyl)silyloxy](cyano)methyl]-3-hydroxypropylcarbamate