(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol

Base Information

Chemical Name:(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol
CAS No.:133604-19-0
Molecular Formula:C₂₄H₃₈O₈S
Molecular Weight:486.627
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol

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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,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol

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Technology Process of (2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol

There total 10 articles about (2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol 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: 71.0%

: 133604-18-9
(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-5-(hydroxymethyl)-4-methyloctane-1,2,3,6,7-pentol

: 124-63-0
methanesulfonyl chloride

: 133604-19-0
(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol

Guidance literature:: With triethylamine; In dichloromethane; at 22 ℃; for 24h;
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

: 133604-19-0
(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol

Guidance literature:: Multi-step reaction with 6 steps

1: 72 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 36 h / 0 °C

2: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 1 h / 22 °C

3: 88 percent / p-TsOH / CH₂Cl₂ / 1 h / 22 °C

4: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to 22 deg C, 5 h

5: 1.) LiAlH₄, 2.) aq. MgSO₄, K₂CO₃ / 1.) diethyl ether, 22 deg C, 3 h, 2.) diethyl ether, 4 h

6: 71 percent / NEt₃ / CH₂Cl₂ / 24 h / 22 °C

With chromium chloride; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; magnesium sulfate; potassium carbonate; toluene-4-sulfonic acid; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00011a025

Reference yield:

: 133604-17-8
(2'R,2S,3S,4S,5R)-4-(benzyloxy)-2-((2',2-isopropylidenedioxy)propyl)-3-methyl-5,6-(isopropylidenedioxy)hexanal

: 133604-19-0
(2R,3S,4S,5R,6R,7S)-3-O-benzyl-1,2:6,7-di-O-isopropylidene-4-methyl-5-O-((methylsulfonyl)methyl)octane-1,2,3,6,7-pentol

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) LiAlH₄, 2.) aq. MgSO₄, K₂CO₃ / 1.) diethyl ether, 22 deg C, 3 h, 2.) diethyl ether, 4 h

2: 71 percent / NEt₃ / CH₂Cl₂ / 24 h / 22 °C

With lithium aluminium tetrahydride; magnesium sulfate; potassium carbonate; triethylamine; In dichloromethane;
DOI:10.1021/ja00011a025