1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone

Base Information

• Chemical Name: 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone
• CAS No.: 85080-95-1
• Molecular Formula: C₉H₁₂O₆
• Molecular Weight: 216.191
• European Community (EC) Number: 285-342-0
• DSSTox Substance ID: DTXSID201174525
• Nikkaji Number: J309.666A

Synonyms:EINECS 285-342-0;85080-95-1;1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone;DTXSID201174525;(1S,2R,6R,8R,9R)-9-Hydroxy-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.0^{2,6}]undecan-10-one;AKOS030242264;1,2-O-Isopropylidene- beta -L-idofuranurono-6,3-lactone;1-O,2-O-(1-Methylethylidene)-beta-D-idofuranuronic acid 6,3-lactone;beta-D-Idofuranuronic acid, 1,2-O-(1-methylethylidene)-, gamma-lactone

Chemical Property of 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone

Chemical Property:

• XLogP3: -0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 216.06338810
• Heavy Atom Count: 15
• Complexity: 314

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C3C(C(C(=O)O3)O)OC2O1)C
• Isomeric SMILES: CC1(O[C@H]2[C@H]3[C@H]([C@@H](C(=O)O3)O)O[C@H]2O1)C

Technology Process of 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone

There total 17 articles about 1,2-O-Isopropylidene-betaD-idofuranurono-6,3-lactone 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: 99.0%

L-glucurono-3,6-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetone (67-64-1) → 1,2-O-isopropylidene-α-L-glucurono-3,6-lactone (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1)

Guidance literature:

With sulfuric acid; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2009.08.124

Reference yield: 97.0%

α-D-glucurono-γ-lactone (14362-29-9) + acetone (67-64-1) → D-glucurono-3,6-lactone acetonide (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1)

Guidance literature:

With sulfuric acid; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2008.10.014

Reference yield: 93.0%

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetone (67-64-1) → D-glucurono-3,6-lactone acetonide (3067-56-9,20513-98-8,25159-39-1,26623-22-3,29514-28-1,85080-95-1)

Guidance literature:

With sulfuric acid;

DOI:10.1016/0008-6215(83)88356-6

upstream raw materials:

D-glucurono-6,3-lactone

O¹,O²-isopropylidene-α-D-glucofuranuronic acid

5-O-acetyl-1,2-O-isopropylidene-β-L-idofuranurono-6,3-lactone

(1S,3R,4R,5S,8S)-8-benzyloxy-7-keto-3,4-isopropylidenedioxy-2,6-dioxabicyclo[3.3.0]octane

Downstream raw materials:

methyl 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranuronate

1,2-O-isopropylidene-5-O-toluene-p-sulphonyl-α-D-glucofuranurono-6,3-lactone

N-(p-methoxybenzyl)-1,2-isopropylidene-D-glucofuranuronamide

(+)-1,2-O-Isopropylidene-5-O-(phenoxythiocarbonyl)-α-D-glucurono-6,3-lactone

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