(S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine

Base Information

• Chemical Name: (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine
• CAS No.: 135582-88-6
• Molecular Formula: C₁₅H₁₉NO₅
• Molecular Weight: 293.32
• Mol file: 135582-88-6.mol

Synonyms:(S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine

Chemical Property of (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine

There total 5 articles about (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-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: 85.0%

(S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate (135582-87-5) + 2,2-dimethoxy-propane (77-76-9) → (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine (135582-88-6)

Guidance literature:

With boron trifluoride diethyl etherate; In acetone; at 25 ℃; for 6.5h; Inert atmosphere;

DOI:10.1002/ejoc.201201413

Reference yield: 84.0%

(S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate (135582-87-5) + acetone (67-64-1) → (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine (135582-88-6)

Guidance literature:

With boron trifluoride diethyl etherate; 2,2-dimethoxy-propane; In acetone; Inert atmosphere;

DOI:10.1021/acsmedchemlett.5b00205

Reference yield:

(2S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxypropanoic acid (42491-79-2) → (S)-3-benzyloxycarbonyl-5-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine (135582-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / methanol; diethyl ether / 0.5 h / 0 °C

2: 65 percent / Et₂O*BF₃ / acetone; diethyl ether / 12 h / Ambient temperature

With boron trifluoride diethyl etherate; In methanol; diethyl ether; acetone;

DOI:10.1055/s-1991-26480

upstream raw materials:

(S)-methyl 3-(benzyloxycarbonylamino)-2-hydroxypropanoate

2,2-dimethoxy-propane

(2S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxypropanoic acid

benzyl chloroformate

Downstream raw materials:

benzyl (S)-5-formyl-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

(R)-3-benzyloxycarbonyl-5-<(Z)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)vinyl>-2,2-dimethyl-1,3-oxazolidine

(R)-3-benzyloxycarbonyl-5-<(S)-N-tert-butoxycarbonylalanin-3-yl>-2,2-dimethyl-1,3-oxazolidine

(R)-3-benzyloxycarbonyl-5-<(S)-2-(tert-butoxycarbonylamino)-2-(methoxycarbonyl)ethyl>-2,2-dimethyl-1,3-oxazolidine