1-O-Benzyl-2C-methyl-3,4-isopropylidine-D-ribopyranoside

Base Information

• Chemical Name: 1-O-Benzyl-2C-methyl-3,4-isopropylidine-D-ribopyranoside
• CAS No.: 569661-37-6
• Molecular Formula: C16H22O5
• Molecular Weight: 294.34
• Mol file: 569661-37-6.mol

Synonyms:1-O-Benzyl-2C-methyl-3,4-isopropylidine-D-ribopyranoside

Chemical Property of 1-O-Benzyl-2C-methyl-3,4-isopropylidine-D-ribopyranoside

Chemical Property:

• Boiling Point: 420.9±45.0 °C(Predicted)
• PKA: 12.91±0.60(Predicted)
• PSA: 57.15000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 1.83060

Purity/Quality:

1-O-BENZYL-2C-METHYL-3,4-ISOPROPYLIDINE-D-RIBOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-O-Benzyl-2C-methyl-3,4-isopropylidine-D-ribopyranoside

There total 4 articles about 1-O-Benzyl-2C-methyl-3,4-isopropylidine-D-ribopyranoside 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: 55.0%

benzyl-3,4-O-isopropylidene-β-D-erythro-pentoribopyranosid-2-ulose (28070-06-6) + methylmagnesium bromide (75-16-1) → 6R-benzyloxy-2,2,7R-trimethyltetrahydro-[1,3]dioxolo[4R,5R-c]pyran-7R-ol (569661-37-6)

Guidance literature:

In diethyl ether; at -78 - -10 ℃;

DOI:10.1002/jhet.5570400221

Reference yield:

benzyl-3,4-O-isopropylidene-β-D-erythro-pentoribopyranosid-2-ulose (28070-06-6) + methyllithium (917-54-4) → 6R-benzyloxy-2,2,7R-trimethyltetrahydro-[1,3]dioxolo[4R,5R-c]pyran-7R-ol (569661-37-6)

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran; diethyl ether; at -20 ℃; for 4h;

DOI:10.1021/ja029225v

Reference yield:

(-)-benzyl β-D-arabinopyranoside (5329-50-0) → 6R-benzyloxy-2,2,7R-trimethyltetrahydro-[1,3]dioxolo[4R,5R-c]pyran-7R-ol (569661-37-6)

Guidance literature:

Multi-step reaction with 3 steps

1: (+/-)camphorsulfonic acid / acetone / 1 h / 25 °C

2: oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / -78 - 0 °C

3: cerium trichloride / tetrahydrofuran; diethyl ether / 4 h / -20 °C

With cerium(III) chloride; oxalyl dichloride; (+/-)camphorsulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 2: Swern oxidation;

DOI:10.1021/ja029225v

upstream raw materials:

benzyl-3,4-O-isopropylidene-β-D-erythro-pentoribopyranosid-2-ulose

methyllithium

methylmagnesium bromide

(-)-benzyl β-D-arabinopyranoside

Downstream raw materials:

benzyl-2-C-methyl-β-D-ribopyranoside

(2R,3R-bis-benzyloxy-3R-methyl-5R-trityloxytetrahydropyran-4R-yloxy)acetic acid tert-butyl ester

(2R,3R,4R,5R)-2,3-Bis-benzyloxy-3-methyl-5-trityloxy-tetrahydro-pyran-4-ol

7R,8R-dibenzyloxy-2S-(2-hydroxy-ethyl)-8R-methyltetrahydropyrano[3R,4R-b][1,4]dioxin-3-one

Refernces

• 1、 Eilitz, Uwe,Boettcher, Christoph,Hennig, Lothar,Burger, Klaus,Haas, Alois,Gockel, Simone,Sieler, Joachim. "Synthesis of homochiral 2-C-trifluoromethyl D- and L-ribose via trifluoromethylation of pentopyranosid-2-uloses". . p. 329 - 335. Retrieved 2007/10/03.