ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate

Base Information

Chemical Name:ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate
CAS No.:952609-66-4
Molecular Formula:C₂₄H₂₈O₅
Molecular Weight:396.483
Hs Code.:

Synonyms:ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate

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Chemical Property of ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate

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Technology Process of ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate

There total 7 articles about ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-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: 69.0%

: 952609-65-3
(4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-tetrahydro-furan-2-carbaldehyde

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 952609-66-4
ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate

Guidance literature:: In benzene; for 1h; Heating;
DOI:10.1016/j.tet.2007.06.110

Reference yield:

: 952609-64-2
((4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-tetrahydro-furan-2-yl)methanol

: 952609-66-4
ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

2: 69 percent / benzene / 1 h / Heating

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; benzene; 1: Swern oxidation;
DOI:10.1016/j.tet.2007.06.110

Reference yield:

: 79364-35-5
(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 952609-66-4
ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / sodium hydride / dimethylformamide; various solvent(s) / 6 h / 0 - 20 °C

2: 84 percent / acetic acid; water / 6 h / 20 °C

3: 68 percent / K₂CO₃; TBAI / acetone / 18 h / Heating

4: 74 percent / m-chloroperbenzoic acid / CHCl₃; H₂O / 6 h / 20 °C

5: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

6: 69 percent / benzene / 1 h / Heating

With oxalyl dichloride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone; benzene; 5: Swern oxidation;
DOI:10.1016/j.tet.2007.06.110