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

Base Information

• Chemical Name: (2S,3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2-hydroxypropyl-1,2,5,6-tetrahydro-4H-1,4-oxazine
• CAS No.: 213687-80-0
• Molecular Formula: C₂₈H₃₁NO₄
• Molecular Weight: 445.558
• Mol file: 213687-80-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about (2S,3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2-hydroxypropyl-1,2,5,6-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: 78.0%

(2S,3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-2(2-propenyl)-1,2,5,6-tetrahydro-4H-1,4-oxazine (213687-08-2) → (2S,3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2-hydroxypropyl-1,2,5,6-tetrahydro-4H-1,4-oxazine (213687-80-0)

Guidance literature:

With sodium hydroxide; (BH₃)2*Me₂S; dihydrogen peroxide; In tetrahydrofuran; methanol; at 20 ℃; for 12h;

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

Reference yield:

(3R,5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazine (213686-69-2) → (2S,3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2-hydroxypropyl-1,2,5,6-tetrahydro-4H-1,4-oxazine (213687-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / TiCl₄ / CH₂Cl₂ / -78 - 0 °C

2: 78 percent / (BH₃)2*Me₂S; NaOH; H₂O₂ / tetrahydrofuran; methanol / 12 h / 20 °C

With sodium hydroxide; (BH₃)2*Me₂S; dihydrogen peroxide; titanium tetrachloride; In tetrahydrofuran; methanol; dichloromethane; 1: Substitution / 2: Oxidation;

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

Reference yield: 66.0%

(2S,3R,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2-hydroxypropyl-1,2,5,6-tetrahydro-4H-1,4-oxazine (213687-80-0) → (2S,3R,5R,6S)-3-(4-benzyloxycarbonyl-5,6-diphenyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-yl)propanoic acid (213687-86-6)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

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

upstream raw materials:

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

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

Downstream raw materials:

(2S,3R,5R,6S)-3-(4-benzyloxycarbonyl-5,6-diphenyl-3-methyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-yl)propanoic acid