(2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine

Base Information

• Chemical Name: (2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine
• CAS No.: 319002-34-1
• Molecular Formula: C₂₉H₃₇NO₆
• Molecular Weight: 495.616
• Mol file: 319002-34-1.mol

Synonyms:(2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine

Chemical Property of (2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine

There total 1 articles about (2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine 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: 83.0%

Triethyl orthoacetate (78-39-7) + [2R,2(1S,2Z),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-1-hydroxy-but-2-enyl)-4-phenyl-1,3-oxazolidine (234122-98-6) → (2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine (319002-34-1)

Guidance literature:

With propionic acid; for 3h; Heating;

DOI:10.1016/S0040-4039(00)01465-9 DOI:10.1002/1099-0690(20021)2002:1<29::AID-EJOC29>3.0.CO;2-B

Reference yield: 68.0%

(2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine (319002-34-1) → (3R,7S,8S,9R)-7-[(1R)-2-benzyloxy-1-ethoxycarbonylmethylethyl]-8-bromo-3-phenyltetrahydrooxazolo[3,2-c][1,3]oxazin-5-one (319002-44-3)

Guidance literature:

With N-Bromosuccinimide; In 1,2-dimethoxyethane; water;

DOI:10.1016/S0040-4039(00)01465-9

Reference yield:

(2R,4R)-2-[(1E,3S)-4-benzyloxy-3-ethoxycarbonylmethylbut-1-enyl]-3-tert-butoxycarbonyl-4-phenyl-1,3-oxazolidine (319002-34-1) → (E)-(S)-3-Benzyloxymethyl-6-oxo-hex-4-enoic acid ethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 1,2-dichloro-ethane / 0.33 h

2: H₂O / tetrahydrofuran / 1 h

With water; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1002/1099-0690(20021)2002:1<29::AID-EJOC29>3.0.CO;2-B

upstream raw materials:

Triethyl orthoacetate

[2R,2(1S,2Z),4R]-3-tert-butoxycarbonyl-2-(4-benzyloxy-1-hydroxy-but-2-enyl)-4-phenyl-1,3-oxazolidine

Downstream raw materials:

(3R,7S,8S,9R)-7-[(1R)-2-benzyloxy-1-ethoxycarbonylmethylethyl]-8-bromo-3-phenyltetrahydrooxazolo[3,2-c][1,3]oxazin-5-one

(2R,4R)-2-[(1R,2R,3R)-4-benzyloxy-1,2-epoxy-3-ethoxycarbonylmethylbutyl]-3-ethoxycarbonyl-4-phenyl-1,3-oxazolidine