(E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate

Base Information

• Chemical Name: (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS No.: 1300690-07-6
• Molecular Formula: C₁₁H₁₈O₅
• Molecular Weight: 230.261
• Mol file: 1300690-07-6.mol

Synonyms:(E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate

Chemical Property of (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate

There total 1 articles about (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate 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: 51.0%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + (-)-dimethy-2,3-O-isopropylidene-L-tartrate (37031-29-1) → (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate (1300690-07-6) + 2,3-O-isopropylidene-L-threitol (50622-09-8) + (E)-3-[(4S,5S)-5-((E)-2-Ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid ethyl ester

Guidance literature:

(-)-dimethy-2,3-O-isopropylidene-L-tartrate; With diisobutylaluminium hydride; In toluene; at 0 ℃; for 3h; Inert atmosphere;

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 1h; Inert atmosphere;

diethoxyphosphoryl-acetic acid ethyl ester; stereoselective reaction; Further stages;

DOI:10.1021/jo200019j

Reference yield: 97.0%

(E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate (1300690-07-6) + tert-butylchlorodiphenylsilane (58479-61-1) → C27H36O5Si

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo200019j

Reference yield: 75.0%

2-benzyloxy-1-methylpyridinium triflate (882980-43-0) + (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate (1300690-07-6) → ethyl 3-((4S,5S)-5-(benzyloxy methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate (90661-38-4,90661-39-5,91548-58-2,91548-59-3)

Guidance literature:

With magnesium oxide; In α,α,α-trifluorotoluene; at 83 ℃; for 66h; Inert atmosphere;

DOI:10.1021/jo200019j

upstream raw materials:

diethoxyphosphoryl-acetic acid ethyl ester

(-)-dimethy-2,3-O-isopropylidene-L-tartrate

Downstream raw materials:

ethyl 3-((4S,5S)-5-(benzyloxy methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

decarestrictine O