(5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

Base Information

• Chemical Name: (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine
• CAS No.: 213686-66-9
• Molecular Formula: C₂₆H₂₅NO₅
• Molecular Weight: 431.488

Synonyms:(5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

Chemical Property of (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

Chemical Property:

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Technology Process of (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine

There total 2 articles about (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine 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:

acetic anhydride (108-24-7) + (2S,3R)-6-Hydroxy-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester → (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (213686-66-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1016/S0040-4020(01)00542-7

Reference yield:

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (105228-46-4,335159-14-3) → (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (213686-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / CH₂Cl₂ / -78 °C

2: Et₃N; DMAP / CH₂Cl₂ / 12 h / 0 - 20 °C

With dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(01)00542-7

Reference yield: 98.0%

(5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (213686-66-9) + allyl-trimethyl-silane (762-72-1) → (2S,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2(2-propenyl)-1,2,5,6-tetrahydro-4H-1,4-oxazine (213686-90-9)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at -15 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(98)00495-5

upstream raw materials:

acetic anhydride

(5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one

Downstream raw materials:

(2S,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2(2-propenyl)-1,2,5,6-tetrahydro-4H-1,4-oxazine

(2S,5R,6S)-2-(4-benzyloxycarbonyl-5,6-diphenyl-1,2,5,6-tetrahydro-4H-1,4-oxazin-2-yl)acetic acid

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