1,6-DI-O-ACETYL-2,3-ISOPROPYLIDENE-D-RIBOSE

Base Information

• Chemical Name: 1,6-DI-O-ACETYL-2,3-ISOPROPYLIDENE-D-RIBOSE
• CAS No.: 141979-56-8
• Molecular Formula: C12H18 O7
• Molecular Weight: 274.27
• Mol file: 141979-56-8.mol

Synonyms:Furo[3,4-d]-1,3-dioxole,D-ribofuranose deriv.

Chemical Property of 1,6-DI-O-ACETYL-2,3-ISOPROPYLIDENE-D-RIBOSE

Chemical Property:

• Vapor Pressure: 9.28E-05mmHg at 25°C
• Refractive Index: 1.485
• Boiling Point: 119°C@0.1mmHg
• Flash Point: 147.5°C
• PSA: 80.29000
• Density: 1.26g/cm³
• LogP: 0.35760
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,5-Di-O-acetyl-2,3-O-isopropylidene-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,5-Di-O-acetyl-2,3-isopropylidene-D-ribose (cas# 141979-56-8) is a compound useful in organic synthesis.

Technology Process of 1,6-DI-O-ACETYL-2,3-ISOPROPYLIDENE-D-RIBOSE

There total 2 articles about 1,6-DI-O-ACETYL-2,3-ISOPROPYLIDENE-D-RIBOSE 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: 97.0%

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) + acetic anhydride (108-24-7) → 1,5-O-diacetyl-2,3-O-isopropylidene-D-ribofuranoside (141979-56-8)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/ja020238i

Reference yield:

D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → 1,5-O-diacetyl-2,3-O-isopropylidene-D-ribofuranoside (141979-56-8)

Guidance literature:

Multi-step reaction with 2 steps

1: H(+)

2: pyridine

With hydrogen cation; In pyridine;

DOI:10.1016/S0040-4039(01)01446-0

Reference yield:

1,5-O-diacetyl-2,3-O-isopropylidene-D-ribofuranoside (141979-56-8) → (S)-2-(4-Methoxy-benzyloxy)-hex-5-enoic acid (S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-butyl ester (442913-67-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TMSOTf / acetonitrile / 24 h / 0 °C

1.2: H₂ / Pd/C / CH₂Cl₂ / 3 h / 20 °C / 760.05 Torr

2.1: 380 mg / MeONa / methanol / 4 h / 20 °C

3.1: 89 percent / iodine; PPh₃; imidazole / CH₂Cl₂ / 20 h / 20 °C

4.1: 86 percent / Zn(Ag)-graphite / tetrahydrofuran / 0.5 h / 20 °C

5.1: 87 percent / DCC; DMAP / CH₂Cl₂ / 28 h / 20 °C

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; iodine; sodium methylate; dicyclohexyl-carbodiimide; triphenylphosphine; silver; zinc; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/ja020238i

upstream raw materials:

2,3-O-isopropylidene-D-ribofuranose

acetic anhydride

D-Ribose

Downstream raw materials:

(E)-(3aS,4S,7S,11aR)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-propyl-3a,4,7,8,9,11a-hexahydro-1,3,5-trioxa-cyclopentacyclodecen-6-one

(S)-2-(4-Methoxy-benzyloxy)-hex-5-enoic acid (S)-1-((4S,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-butyl ester

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose

(3aR,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

Refernces

• 1、 Ray, Debarpita,Beuning, Penny J.,Ondrechen, Mary Jo,O'Doherty, George A.. "A practical synthesis of glycinamide ribonucleotide". . p. 776 - 784. Retrieved 2019/04/26.
• 2、 Solarte, Carmen,Dos Santos, Micha?l,Gonzalez, Simon,Miranda, Leandro S. M.,Guillot, Régis,Ferry, Angélique,Gallier, Florian,Uziel, Jacques,Lubin-Germain, Nadège. "Synthesis of C -Ribosyl-1,2,3-triazolyl Carboxamides". . p. 1993 - 2002. Retrieved 2017/04/26.