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

Base Information

• Chemical Name: 1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol
• CAS No.: 291313-64-9
• Molecular Formula: C₂₀H₂₈O₆
• Molecular Weight: 364.439
• Mol file: 291313-64-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about 1D-6-O-benzyl-3-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%

1D-6-O-benzyl-3-deoxy-1,2:4,5-di-O-isopropylidene-3-methylene-myo-inositol (290812-74-7) → 1L-3-O-benzyl-6-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol (290812-40-7) + 1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol (291313-64-9)

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

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: 42 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:

(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 (192122-41-1) → 1D-6-O-benzyl-3-deoxy-6-(hydroxymethyl)-1,2:4,5-di-O-isopropylidene-chiro-inositol (291313-64-9)

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: 42 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

upstream raw materials:

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

(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

Downstream raw materials:

(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-3-deoxy-3-hydroxymethyl-myo-inositol

(3aR,4R,5R,6S,7R,7aR)-4-Allyloxymethyl-7-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5,6-diol

(1R,2R,3S,4R,5S,6S)-3-Allyloxymethyl-4,5,6-tris-benzyloxy-cyclohexane-1,2-diol

[(R)-((3aR,4R,4aR,7aR,8R,8aS)-8-Benzyloxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl)-hydroxy-methyl]-phosphonic acid dibenzyl ester