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

Base Information

• Chemical Name: Methyl-5-deoxy-2,3-O-isopropylidene-D-ribofuranoside
• CAS No.: 78341-97-6
• Molecular Formula: C9H16 O4
• Molecular Weight: 188.224
• Hs Code.: 2932999099
• Mol file: 78341-97-6.mol

Synonyms:Ribofuranoside,methyl 5-deoxy-2,3-O-isopropylidene-, D- (6CI); Furo[3,4-d]-1,3-dioxole,D-ribofuranoside deriv.

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

Chemical Property:

• Boiling Point: 73-75 °C(Press: 12 Torr)
• PSA: 36.92000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 0.89770

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-Deoxy-2,3-O-(1-methylethylidene)-D-ribofuranoside Methyl Ether is an intermediate in the synthesis of Capecitabine (C175650) related compounds.

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

There total 7 articles about Methyl-5-deoxy-2,3-O-isopropylidene-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: 95.0%

(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole (50600-40-3) → 1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose (78341-97-6)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; at 20 ℃; for 24h; Inert atmosphere;

Reference yield: 90.0%

(3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole (78341-96-5) → 1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose (78341-97-6)

Guidance literature:

With potassium hydroxide; hydrogen; palladium on activated charcoal; In methanol; for 15h; Ambient temperature;

DOI:10.1002/hlca.19820650525

Reference yield:

((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate (4137-56-8,5531-22-6,6953-71-5,52631-00-2,63087-95-6,84894-43-9,13007-50-6) → 1-O-methyl-2,3-O-isopropylidene-5-deoxy-D-ribofuranose (78341-97-6)

Guidance literature:

((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl 4-methylbenzenesulfonate; With sodium tetrahydroborate; In dimethyl sulfoxide; at 80 - 85 ℃; Inert atmosphere;

With acetic acid; In dimethyl sulfoxide; at 10 - 30 ℃;

upstream raw materials:

(3aS,4S,6aR)-4-(bromomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

(3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole

methyl 2,3-O-isopropylidene-D-ribofuranoside

D-Ribose

Downstream raw materials:

L-5-deoxy-lyxose

(2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol

C₁₇H₂₅FN₄O₈

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