(R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane

Base Information

• Chemical Name: (R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane
• CAS No.: 207679-23-0
• Molecular Formula: C₁₆H₂₂O₅
• Molecular Weight: 294.348
• Mol file: 207679-23-0.mol

Synonyms:(R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane

Chemical Property of (R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane

There total 3 articles about (R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane 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: 84.0%

p-Methoxybenzyl bromide (2746-25-0) + (1S,2R)-2-(methoxymethoxy)-1-((R)-oxiran-2-yl)but-3-en-1-ol (207679-21-8) → (R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane (207679-23-0)

Guidance literature:

With sodium hydride; at 25 ℃;

DOI:10.1021/ja9801386

Reference yield:

(3R,4R)-4-(methoxymethoxy)hexa-1,5-dien-3-ol (112531-79-0) → (R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane (207679-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / L-(+)-DIPT; t-BuOOH; Ti(O-i-Pr)4 / -10 °C

2: 84 percent / NaH

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; sodium hydride; 1: asymmetric epoxidation / 2: Alkylation;

DOI:10.1021/ja992274w

Reference yield:

[(Z)-γ-(methoxymethoxy)allyl]-(-)-diisopinocampheylborane (112482-56-1) → (R)-2-[(1S,2R)-1-(4-Methoxy-benzyloxy)-2-methoxymethoxy-but-3-enyl]-oxirane (207679-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / BF₃*Et₂O

2: 90 percent / L-(+)-DIPT; t-BuOOH; Ti(O-i-Pr)4 / -10 °C

3: 84 percent / NaH

With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; boron trifluoride diethyl etherate; sodium hydride; 1: Addition / 2: asymmetric epoxidation / 3: Alkylation;

DOI:10.1021/ja992274w

upstream raw materials:

p-Methoxybenzyl bromide

(1S,2R)-2-(methoxymethoxy)-1-((R)-oxiran-2-yl)but-3-en-1-ol

(3R,4R)-4-(methoxymethoxy)hexa-1,5-dien-3-ol

[(Z)-γ-(methoxymethoxy)allyl]-(-)-diisopinocampheylborane

Downstream raw materials:

(S)-2-[(E)-(1R,2S)-2-Acetoxy-4-acetylamino-3-bromo-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

(S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

(S)-2-[(Z)-(1R,2R)-2-Acetoxy-4-acetylamino-1-(4-methoxy-benzyloxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester