(3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran

Base Information

Chemical Name:(3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran
CAS No.:524722-50-7
Molecular Formula:C₂₁H₂₂O₃
Molecular Weight:322.404
Hs Code.:

Synonyms:(3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran

Chemical Property:

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Technology Process of (3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran

There total 7 articles about (3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran 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: 93.0%

: (2R,3S,4R,5S)-3,4-Bis-benzyloxy-2-iodomethyl-5-vinyl-tetrahydro-furan

: 524722-50-7
(3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 90 ℃;
DOI:10.1016/S0040-4020(02)01402-3

Reference yield:

: 2,3,4-tri-O-benzyl-6-O-(4-methoxybenzyl)-α,β-D-glucopyranose

: 524722-50-7
(3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran

Guidance literature:: Multi-step reaction with 7 steps

1.1: BuLi / 1,2-dimethoxy-ethane; hexane / 3 h / 20 °C

1.2: 66 percent / BuLi / 1,2-dimethoxy-ethane; hexane / 0.33 h / 0 - 80 °C

2.1: pyridine / CH₂Cl₂ / 4 h / -40 - -20 °C

3.1: 1.08 g / CH₂Cl₂ / -20 - 20 °C

4.1: 87 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 20 °C

5.1: 87 percent / 4-dimethylaminopyridine / pyridine / 24 h / 20 °C

6.1: NaI; Bu₄NI; molecular sieves 4 Angstroem / dimethylsulfoxide / 7 h / 80 °C

7.1: 93 percent / DBU / dimethylsulfoxide / 90 °C

With pyridine; dmap; n-butyllithium; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In pyridine; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; 1.2: Wittig olefination;
DOI:10.1016/S0040-4020(02)01402-3

Reference yield:

: 524722-61-0
4,5-di-O-benzyl-3,6-anhydro-L-ido-hept-1-enitol

: 524722-50-7
(3S,4R,5S)-3,4-di-benzyloxy-2-methylene-5-vinyltetrahydrofuran

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / 4-dimethylaminopyridine / pyridine / 24 h / 20 °C

2: NaI; Bu₄NI; molecular sieves 4 Angstroem / dimethylsulfoxide / 7 h / 80 °C

3: 93 percent / DBU / dimethylsulfoxide / 90 °C

With dmap; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In pyridine; dimethyl sulfoxide;
DOI:10.1016/S0040-4020(02)01402-3