(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

Base Information

Chemical Name:(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
CAS No.:133604-18-9
Molecular Formula:C₂₃H₃₆O₆
Molecular Weight:408.535
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 9 articles about (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 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

: 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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 133604-43-0,133695-41-7
(E)-(4S,5S)-5-Benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-en-1-ol

: 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

Guidance literature:: Multi-step reaction with 6 steps

1: PBr₃ / diethyl ether / 2 h / 22 °C

2: 72 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 36 h / 0 °C

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

4: 88 percent / p-TsOH / CH₂Cl₂ / 1 h / 22 °C

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

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

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

Reference yield:

: 120040-77-9,133604-44-1
(2R,3S)-3-Benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-propionaldehyde

: 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

Guidance literature:: Multi-step reaction with 8 steps

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

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

3: PBr₃ / diethyl ether / 2 h / 22 °C

4: 72 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 36 h / 0 °C

5: 90 percent / Bu₄NF*3H₂O / tetrahydrofuran / 1 h / 22 °C

6: 88 percent / p-TsOH / CH₂Cl₂ / 1 h / 22 °C

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

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

With chromium chloride; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; phosphorus tribromide; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; potassium carbonate; toluene-4-sulfonic acid; ozone; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja00011a025