Methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside

Base Information

• Chemical Name: Methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside
• CAS No.: 23202-81-5
• Molecular Formula: C9H16O4
• Molecular Weight: 188.224
• Hs Code.: 2932999099
• European Community (EC) Number: 245-485-1
• DSSTox Substance ID: DTXSID20177783
• Nikkaji Number: J318.424B
• Wikidata: Q72489853
• Mol file: 23202-81-5.mol

Synonyms:23202-81-5;Methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside;(3aR,4R,6R,6aR)-4-methoxy-2,2,6-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole;EINECS 245-485-1;Methyl-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside;beta-D-Ribofuranoside, methyl 5-deoxy-2,3-O-(1-methylethylidene)-;EC 245-485-1;(3AR,4R,6r,6aR)-4-methoxy-2,2,6-trimethyltetrahydrofuro[3,4-d][1,3]dioxole;SCHEMBL3459775;RNHBZJGMAYMLBE-WCTZXXKLSA-;DTXSID20177783;MFCD08703329;AKOS006289288;BS-16720;F20817;b-D-Ribofuranoside, methyl5-deoxy-2,3-O-(1-methylethylidene)-;Methyl 2-O,3-O-isopropylidene-5-deoxy-beta-D-ribofuranoside;Methyl-5-deoxy-2,3- O C isopropylidene-|A-D- ribofuranoside;(3aR,4R,6R,6aR)-4-methoxy-2,2,6-trimethyl-3a,4,6,6a-tetrahydrofuro[4,3-d][1,3]dioxole

Chemical Property of Methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside

Chemical Property:

• Vapor Pressure: 0.128mmHg at 25°C
• Refractive Index: 1.465
• Boiling Point: 225.623 °C at 760 mmHg
• Flash Point: 88.612 °C
• PSA: 36.92000
• Density: 1.12 g/cm³
• LogP: 0.89770
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 188.10485899
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

99% ^*data from raw suppliers

Methyl 5-deoxy-2,3-O-isopropylidene-b-D-ribofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2C(C(O1)OC)OC(O2)(C)C
• Isomeric SMILES: C[C@@H]1[C@@H]2[C@H]([C@@H](O1)OC)OC(O2)(C)C
• Uses: Methyl-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside is an impurity of Capecitabine(C175650) which is an antineoplastic agent. Capecitabine is a prodrug of Doxifluridine (D556750).

Technology Process of Methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside

There total 24 articles about Methyl 5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside 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: 100.0%

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside (4137-56-8) → methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside (23202-81-5)

Guidance literature:

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside; With sodium tetrahydroborate; In dimethyl sulfoxide; at 85 ℃; for 13h;

With ammonium chloride; In dimethyl sulfoxide;

Reference yield: 95.0%

methyl (1R,2R,3R,4R)-2,3-O-isopropylidene-5-O-trifluoromethanesulfonyl-beta-D-ribofuranoside (70209-11-9) → methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside (23202-81-5)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0008-6215(02)00464-0

Reference yield: 90.0%

1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside (50610-99-6,75100-24-2,81026-76-8,96896-28-5) → methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside (23202-81-5)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In diethylene glycol dimethyl ether; at 80 - 90 ℃; for 20h; Solvent; Reagent/catalyst; Temperature;

DOI:10.1021/acs.oprd.5b00286

upstream raw materials:

methyl 5-deoxy-5-iodo-2,3-isopropylidene-β-D-ribofuranoside

Methyl 5-O-acetyl-2,3-O-isopropylidene-β-D-ribofuranoside

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside

1-O-methyl-2,3-O-isopropylidene-5-bromo-5-deoxy-β-D-ribofuranoside

Downstream raw materials:

5′-deoxyribose

5-O-deoxy-D-ribofuranose

1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose

capecitabine