(2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

Base Information

Chemical Name:(2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol
CAS No.:133604-08-7
Molecular Formula:C₂₅H₃₂O₄
Molecular Weight:396.527
Hs Code.:

Synonyms:(2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

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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 (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

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Technology Process of (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

There total 8 articles about (2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol 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:

: 128632-65-5
(R)-4-((E)-(1S,2S)-1-Benzyloxy-5-bromo-2-methyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane

: 100-52-7
benzaldehyde

: 133604-08-7
(2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

: 133604-08-7
(2R,3S,4S,5R,6S)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

Guidance literature:: With chromium chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 36h; Yield given. Yields of byproduct given;
DOI:10.1021/ja00011a025

Reference yield:

: 128632-65-5
(R)-4-((E)-(1S,2S)-1-Benzyloxy-5-bromo-2-methyl-pent-3-enyl)-2,2-dimethyl-[1,3]dioxolane

: 100-52-7
benzaldehyde

: 133604-08-7
(2R,3S,4S,5S,6R)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

: 133604-08-7
(2R,3S,4S,5R,6S)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

Guidance literature:: With chromium chloride; lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 36h; Yield given. Yields of byproduct given;
DOI:10.1021/ja00011a025

Reference yield:

: 100572-69-8
(2R,3S,4S)-3-Bnzyloxy-1,2-O-isopropylidene-4-methyl-5-hexene-1,2-diol

: 133604-08-7
(2R,3S,4S,5R,6S)-3-O-benzyl-1,2-O-isopropylidene-4-methyl-6-phenyl-5-vinylhexane-1,2,3,6-tetrol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂

2: 1.) NaH / 1.) THF, RT, 2 h, 2.) RT, 24 h

3: DIBAH / toluene; diethyl ether / 4 h / -5 °C

4: PBr₃ / diethyl ether / 2 h / 22 °C

5: CrCl₃, LiAlH₄ / tetrahydrofuran / 36 h / 0 °C

With chromium chloride; lithium aluminium tetrahydride; phosphorus tribromide; sodium hydride; diisobutylaluminium hydride; ozone; triphenylphosphine; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1021/ja00011a025