1,2:5,6-Di-O-isopropylidene-D-glucitol

Base Information

• Chemical Name: 1,2:5,6-Di-O-isopropylidene-D-glucitol
• CAS No.: 53735-98-1
• Molecular Formula: C12H22 O6
• Molecular Weight: 262.303
• European Community (EC) Number: 258-736-5
• DSSTox Substance ID: DTXSID301282741
• Nikkaji Number: J296.035D
• Mol file: 53735-98-1.mol

Synonyms:53735-98-1;1,2:5,6-Di-O-isopropylidene-D-glucitol;SCHEMBL4022246;DTXSID301282741;1-O,2-O:5-O,6-O-Diisopropylidene-D-glucitol

Chemical Property of 1,2:5,6-Di-O-isopropylidene-D-glucitol

Chemical Property:

• Vapor Pressure: 2.08E-07mmHg at 25°C
• Boiling Point: 382°C at 760 mmHg
• Flash Point: 184.8°C
• PSA: 77.38000
• Density: 1.175g/cm³
• LogP: 0.01120
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 262.14163842
• Heavy Atom Count: 18
• Complexity: 273

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OCC(O1)C(C(C2COC(O2)(C)C)O)O)C
• Isomeric SMILES: CC1(OC[C@@H](O1)[C@H]([C@@H]([C@@H]2COC(O2)(C)C)O)O)C

Technology Process of 1,2:5,6-Di-O-isopropylidene-D-glucitol

There total 15 articles about 1,2:5,6-Di-O-isopropylidene-D-glucitol 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: 95.6%

C26H30O8 (71240-80-7,96149-47-2,99828-25-8,107243-32-3) → (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (53735-98-1)

Guidance literature:

With sodium methylate; In methanol; for 28h; Ambient temperature;

DOI:10.1016/S0008-6215(00)81892-3

Reference yield: 83.3%

mannitol (69-65-8) + 2,2-dimethoxy-propane (77-76-9) → (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (53735-98-1)

Guidance literature:

With ethane; propane; tin(ll) chloride; at 25 ℃; for 1.5h; Reflux; Industrial scale;

Reference yield: 60.0%

D-sorbitol (50-70-4) + 2,2-dimethoxy-propane (77-76-9) → (1S,2S)-1,2-bis[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol (53735-98-1)

Guidance literature:

With toluene-4-sulfonic acid; In dimethyl sulfoxide; for 48h; Ambient temperature;

upstream raw materials:

D-sorbitol

C₂₆H₃₀O₈

2,2-dimethoxy-propane

1,2-isopropylidene-D-glucitol

Downstream raw materials:

O³,O⁴-dibenzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-glucitol

Glyceraldehyde

(d,l) isopropylidene glyceraldehyde

2,3-isopropylidene-glyceraldehyde

Refernces

SOME ASPECTS OF THE ISOPROPYLIDENATION OF D-GLUCITOL UNDER NEUTRAL CONDITIONS

10.1016/S0008-6215(00)81892-3

The research investigates the isopropylidenation of D-glucitol under neutral conditions, aiming to study the reaction mechanism and improve the isolation procedure for the main equilibrium product, 1,2:5,6-di-O-isopropylidene-D-glucitol. The findings reveal that the reaction produces various products, including the major diacetal 6, and that the presence of water can inhibit the reaction. The research concludes that the acetal-exchange reaction under neutral conditions is similar to zinc chloride catalysis in terms of product distribution but differs from acid-catalysed isopropylidenation. An improved isolation procedure involving crystallisation or formation of the 3,4-dibenzoate followed by debenzoylation is described, yielding the diacetal 6 with higher efficiency.