1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

Base Information

Chemical Name:1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol
CAS No.:290812-40-7
Molecular Formula:C₂₀H₂₈O₆
Molecular Weight:364.439
Hs Code.:

Synonyms:1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

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Chemical Property of 1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

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Technology Process of 1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

There total 3 articles about 1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol 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: 48.0%

: 290812-74-7
1D-6-O-benzyl-3-deoxy-1,2:4,5-di-O-isopropylidene-3-methylene-myo-inositol

: 290812-40-7
1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

: 291313-64-9
1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

Guidance literature:: 1D-6-O-benzyl-3-deoxy-1,2:4,5-di-O-isopropylidene-3-methylene-myo-inositol; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 50 ℃; for 2h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; ethanol; at 50 ℃; for 1h; Further stages.;
DOI:10.1021/jm000117y

Reference yield:

: (3aS,4aS,7aR,8S,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-one

: 290812-40-7
1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / 0 °C

1.2: 54 percent / tetrahydrofuran / -78 - 20 °C

2.1: 9-BBN / tetrahydrofuran / 2 h / 50 °C

2.2: 48 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 1 h / 50 °C

With 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; In tetrahydrofuran; 1.1: Metallation / 1.2: Methylenation / 2.1: Hydroboration / 2.2: Oxidation;
DOI:10.1021/jm000117y

Reference yield:

: 192122-41-1
(3aR,4R,4aR,7aR,8S,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol

: 290812-40-7
1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol

Guidance literature:: Multi-step reaction with 3 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / 2 h / -78 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / 0 °C

2.2: 54 percent / tetrahydrofuran / -78 - 20 °C

3.1: 9-BBN / tetrahydrofuran / 2 h / 50 °C

3.2: 48 percent / aq. NaOH; H₂O₂ / tetrahydrofuran; ethanol / 1 h / 50 °C

With 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Methylenation / 3.1: Hydroboration / 3.2: Oxidation;
DOI:10.1021/jm000117y