(2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol
CAS No.:120594-97-0
Molecular Formula:C₁₈H₂₆O₄
Molecular Weight:306.402
Hs Code.:

Synonyms:(2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol

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Chemical Property of (2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol

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Technology Process of (2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol

There total 8 articles about (2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-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: 100.0%

: 108507-27-3
(E)-3-((2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-3-hydroxy-2,4-dimethyl-tetrahydro-furan-2-yl)-acrylic acid ethyl ester

: 120594-97-0
(2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol

Guidance literature:: With diisobutylaluminium hydride; at -78 ℃; for 1h;
DOI:10.1016/S0040-4020(01)89819-7

Reference yield:

: 108469-97-2
(E)-(4R,5R)-4-Benzyloxy-5-methoxymethoxy-2,4-dimethyl-hept-2-en-1-ol

: 120594-97-0
(2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / mCPBA / CH₂Cl₂ / - 30 deg C, 7 h, - 20 deg C, 18 h,

2: 1.) DMSO, oxalyl chloride 2.) Et₃N / 1.) DMSO, oxalyl chloride, CH₂Cl₂, - 50 deg C, 15 min 2.) Et₃N, warm to room temp

3: 93 percent / benzene / 1 h / Ambient temperature

4: 94 percent / TFA / CHCl₃ / 0.17 h / Ambient temperature

5: 100 percent / DIBAL-H / 1 h / -78 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; chloroform; benzene;
DOI:10.1016/S0040-4020(01)89819-7

Reference yield:

: 108469-96-1
(E)-(4R,5R)-4-Benzyloxy-5-hydroxy-2,4-dimethyl-hept-2-enoic acid methyl ester

: 120594-97-0
(2S,3S,4R,5R)-4-Benzyloxy-5-ethyl-2-((E)-3-hydroxy-propenyl)-2,4-dimethyl-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / P₂O₅ / CHCl₃ / 0.5 h / Ambient temperature

2: 100 percent / DIBAL-H / tetrahydrofuran / 1.5 h / -78 °C

3: 90 percent / mCPBA / CH₂Cl₂ / - 30 deg C, 7 h, - 20 deg C, 18 h,

4: 1.) DMSO, oxalyl chloride 2.) Et₃N / 1.) DMSO, oxalyl chloride, CH₂Cl₂, - 50 deg C, 15 min 2.) Et₃N, warm to room temp

5: 93 percent / benzene / 1 h / Ambient temperature

6: 94 percent / TFA / CHCl₃ / 0.17 h / Ambient temperature

7: 100 percent / DIBAL-H / 1 h / -78 °C

With oxalyl dichloride; phosphorus pentoxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; benzene;
DOI:10.1016/S0040-4020(01)89819-7