(+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol

Base Information

• Chemical Name: (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol
• CAS No.: 6691-27-6
• Molecular Formula: C₄₀H₄₄O₆
• Molecular Weight: 620.786
• Mol file: 6691-27-6.mol

Synonyms:

Chemical Property of (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol

There total 11 articles about (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-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: 93.0%

rac-1,2-O-cyclohexylidene-myo-inositol (6763-47-9,1251832-23-1) + benzyl bromide (100-39-0) → (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol (6691-27-6,57029-85-3,57029-86-4,130324-54-8)

Guidance literature:

rac-1,2-O-cyclohexylidene-myo-inositol; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 16h; Reflux; Inert atmosphere;

DOI:10.1016/j.tet.2010.11.063

Reference yield:

D-myo-inositol (87-89-8) → (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol (6691-27-6,57029-85-3,57029-86-4,130324-54-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-TsOH / dimethylformamide; toluene / 10 h / 122 - 136 °C

1.2: 98 percent / p-TsOH; EtOH / 48 h / 20 °C

2.1: KOH / 2 h / 115 - 131 °C

With potassium hydroxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene; 1.1: Condensation / 1.2: alcoholysis / 2.1: Alkylation;

DOI:10.1016/0008-6215(96)00043-2

Reference yield:

rac-1,2-O-cyclohexylidene-myo-inositol (6763-47-9,1251832-23-1) + benzyl chloride (100-44-7) → (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol (6691-27-6,57029-85-3,57029-86-4,130324-54-8)

Guidance literature:

With potassium hydroxide; at 120 ℃; for 0.5h;

DOI:10.1002/hlca.19900730428

upstream raw materials:

rac-1,2-O-cyclohexylidene-myo-inositol

benzyl bromide

benzyl chloride

(+/-)-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol

Downstream raw materials:

rac-1,4,5,6-tetra-O-benzyl-myo-inositol

1,2,3,4,5,6-hexa-O-benzyl-myo-inositol

meso-1,3,4,5,6-penta-O-benzyl-myo-inositol

2-O-(myo-inositol-2-phosphoryl)-L-ascorbic acid