(2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol

Base Information

• Chemical Name: (2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol
• CAS No.: 124871-85-8
• Molecular Formula: C₂₄H₃₂O₅
• Molecular Weight: 400.515
• Mol file: 124871-85-8.mol

Synonyms:(2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol

Chemical Property of (2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol

There total 5 articles about (2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-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: 99.0%

(2E,4S,5R)-4-benzyloxy-2,4-dimethyl-5-(4-methoxybenzyloxy)hepta-2-en-1-ol (124871-84-7) → (2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol (124871-85-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; -20 deg C, 7 h, 0 deg C, 3 h;

DOI:10.1248/cpb.37.1155

Reference yield:

(2S,3R)-3-[(1R,2R)-1-Benzyloxy-2-(4-methoxy-benzyloxy)-1-methyl-butyl]-2-(4-methoxy-benzyloxymethyl)-2-methyl-oxirane → (2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol (124871-85-8) + (2R,3R)-2-Benzyloxy-2-[(2R,3S)-3-(4-methoxy-benzyloxymethyl)-3-methyl-oxiranyl]-pentan-3-ol

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 0.166667h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/S0040-4039(01)91293-6

Reference yield:

(2E,4S,5R)-4-benzyloxy-1-hydroxy-2,4-dimethylhept-2-ene (98004-01-4) → (2S,3R,4R,5R)-4-benzyloxy-2,4-dimethyl-2,3-epoxy-5-(4-methoxybenzyloxy)heptan-1-ol (124871-85-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / CSA / benzene / 0.17 h / Ambient temperature

2: 1.) NaH, 2.) 10percent HCl / 1.) DMF, RT, 24 h, 2.) H₂O, CH₂Cl₂, RT, 30 min

3: 99 percent / m-CPBA / CH₂Cl₂ / -20 deg C, 7 h, 0 deg C, 3 h

With hydrogenchloride; camphor-10-sulfonic acid; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;

DOI:10.1248/cpb.37.1155

upstream raw materials:

(2E,4S,5R)-4-benzyloxy-2,4-dimethyl-5-(4-methoxybenzyloxy)hepta-2-en-1-ol

(2E,4S,5R)-4-benzyloxy-1-hydroxy-2,4-dimethylhept-2-ene

(2E,4S,5R)-4-benzyloxy-5-hydroxy-1-(1-methoxy-1-methylethyl)-2,4-dimethyl-2-heptene

p-methoxybenzyl chloride

Downstream raw materials:

(2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane

(2S,3R,4S,5R)-4-benzyloxy-2,4-dimethyl-5-(4-methoxybenzyloxy)-heptane-1,3-diol