(R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

Base Information

• Chemical Name: (R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester
• CAS No.: 199465-72-0
• Molecular Formula: C₁₄H₁₅NO₅
• Molecular Weight: 277.277

Synonyms:(R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

Chemical Property of (R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

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Technology Process of (R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

There total 2 articles about (R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl 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:

(E)-2,4-pentadienoic acid (21651-12-7) → (R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (199465-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / chloro-nitroso compound / CH₂Cl₂; ethanol / -10 deg C, 16 h; 0 deg C, 3 h

2: NaHCO₃ / methanol / 5 h / Ambient temperature

With sodium hydrogencarbonate; nitrosylchloride; In methanol; ethanol; dichloromethane;

DOI:10.1002/hlca.19980810550

Reference yield:

methanol (67-56-1) + benzyl chloroformate (501-53-1,94274-21-2) + (R)-3,6-Dihydro-2H-[1,2]oxazine-6-carboxylic acid; hydrochloride → (R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (199465-72-0)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate;

DOI:10.1055/s-1997-5794

Reference yield: 14.0%

(R)-3,6-Dihydro-[1,2]oxazine-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (199465-72-0) → (4R,5R,6R)-4,5-Dihydroxy-[1,2]oxazinane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (199465-73-1) + (4S,5S,6R)-4,5-Dihydroxy-[1,2]oxazinane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester (199465-74-2)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; at 40 ℃; for 5h;

DOI:10.1002/hlca.19980810550

upstream raw materials:

methanol

benzyl chloroformate

(E)-2,4-pentadienoic acid

Downstream raw materials:

(4R,5R,6R)-4,5-Dihydroxy-[1,2]oxazinane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

(4S,5S,6R)-4,5-Dihydroxy-[1,2]oxazinane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

(R)-3,7-Dioxa-4-aza-bicyclo[4.1.0]heptane-2,4-dicarboxylic acid 4-benzyl ester 2-methyl ester

(4S,5R,6R)-4,5-Dihydroxy-[1,2]oxazinane-2,6-dicarboxylic acid 2-benzyl ester 6-methyl ester

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