(1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol

Base Information

• Chemical Name: (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol
• CAS No.: 191489-11-9
• Molecular Formula: C₁₃H₁₅N₃O₃
• Molecular Weight: 261.28
• Mol file: 191489-11-9.mol

Synonyms:(1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol

Chemical Property of (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol

There total 3 articles about (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol 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: 62.0%

(5R,6S)-5-azido-6-benzyloxycyclohex-2-en-1-ol → (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol (191489-11-9) + (1S,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 22h;

DOI:10.1016/S0008-6215(97)00021-9

Reference yield:

(2S,3R,5R)-3-Azido-2-benzyloxy-5-hydroxycyclohexanone (171074-21-8) → (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol (191489-11-9)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; methanesulfonyl chloride / 4 h / 0 - 20 °C

2: 70 percent / CsCl₃*6H₂O; NaBH₄ / methanol / 3 h / 0 °C

3: 62 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 22 h / 20 °C

With pyridine; sodium tetrahydroborate; CsCl₃*6H₂O; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; 1: Elimination / 2: Reduction / 3: Epoxidation;

DOI:10.1016/S0008-6215(97)00021-9

Reference yield:

(5R,6S)-5-azido-6-benzyloxycyclohex-2-enone (325959-69-1) → (1R,2S,3R,5S,6R)-3-azido-2-benzyloxy-5,6-epoxycyclohexan-1-ol (191489-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / CsCl₃*6H₂O; NaBH₄ / methanol / 3 h / 0 °C

2: 62 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 22 h / 20 °C

With sodium tetrahydroborate; CsCl₃*6H₂O; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; 1: Reduction / 2: Epoxidation;

DOI:10.1016/S0008-6215(97)00021-9

upstream raw materials:

(2S,3R,5R)-3-Azido-2-benzyloxy-5-hydroxycyclohexanone

(5R,6S)-5-azido-6-benzyloxycyclohex-2-enone