4,7-Bis(benzyloxy)-2,2-dimethylhexahydro-2H-1,3-benzodioxole-5,6-diol

Base Information

• Chemical Name: 4,7-Bis(benzyloxy)-2,2-dimethylhexahydro-2H-1,3-benzodioxole-5,6-diol
• CAS No.: 142435-92-5
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472
• DSSTox Substance ID: DTXSID30551898
• Mol file: 142435-92-5.mol

Synonyms:142435-92-5;DL-1,6-bis-o-(1-Methylethylidene)-2,5-bis-o-(phenylmethyl)-myo-inositol;4,7-Bis(benzyloxy)-2,2-dimethylhexahydro-2H-1,3-benzodioxole-5,6-diol;2,2-dimethyl-4,7-bis(phenylmethoxy)-3a,4,5,6,7,7a-hexahydro-1,3-benzodioxole-5,6-diol;5,6-O-(1-Methylethylidene)-1,4-bis-O-(phenylmethyl)-myo-inositol;DTXSID30551898

Chemical Property of 4,7-Bis(benzyloxy)-2,2-dimethylhexahydro-2H-1,3-benzodioxole-5,6-diol

Chemical Property:

• PSA: 77.38000
• LogP: 2.41270
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 400.18858861
• Heavy Atom Count: 29
• Complexity: 470

Purity/Quality:

97% ^*data from raw suppliers

DL-1,6-bis-o-(1-Methylethylidene)-2,5-bis-o-(phenylmethyl)-myo-inositol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(O1)C(C(C(C2OCC3=CC=CC=C3)O)O)OCC4=CC=CC=C4)C

Technology Process of 4,7-Bis(benzyloxy)-2,2-dimethylhexahydro-2H-1,3-benzodioxole-5,6-diol

There total 20 articles about 4,7-Bis(benzyloxy)-2,2-dimethylhexahydro-2H-1,3-benzodioxole-5,6-diol 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%

benzyl bromide (100-39-0) + (+/-)-1,2-O-isopropylidene-myo-inositol (6404-82-6,13035-67-1,26276-97-1,65795-25-7,113972-96-6,113973-63-0,128387-20-2,149820-68-8) → (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol (98906-25-3,114297-83-5,117307-15-0,142435-92-5,173828-64-3)

Guidance literature:

(+/-)-1,2-O-isopropylidene-myo-inositol; With di(n-butyl)tin oxide; In methanol; toluene; at 130 ℃; for 3h;

benzyl bromide; With tetrabutylammomium bromide; In toluene; at 130 ℃; for 6h;

DOI:10.1021/jo026794c

Reference yield: 80.0%

(+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol (58706-20-0,58769-26-9,98974-90-4,142435-95-8) → (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol (98906-25-3,114297-83-5,117307-15-0,142435-92-5,173828-64-3)

Guidance literature:

With toluene-4-sulfonic acid; ethylene glycol; triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1039/a608337d

Reference yield: 57.0%

(±)-2,3:5,6-di-O-isopropylidene-1,4-di-O-benzyl-myo-inositol → (±)-1,2-O-isopropylidene-3,6-di-O-benzyl-myo-inositol (98906-25-3,114297-83-5,117307-15-0,142435-92-5,173828-64-3)

Guidance literature:

With sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In water; acetone; for 6h;

DOI:10.1016/j.ejmech.2015.01.064

upstream raw materials:

(+/-)-3,6-di-O-benzyl-1,2:4,5-di-O-isopropylidene-myo-inositol

(±)-1,4-di-O-benzyl-myo-inositol

2,2-dimethoxy-propane

benzyl bromide

Downstream raw materials:

(+/-)-3,6-di-O-benzyl-4,5-di-O-butyryl-1,2-O-isopropylidene-myo-inositol

(+/-)-3,4,6-tri-O-benzyl-1,2-O-isopropylidene-myo-inositol

(+/-)-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-myo-inositol

(3aR,4S,5R,6S,7S,7aR)-6-Allyloxy-4,7-bis-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-ol