Methyl 3,5-di-O-benzyl-D-ribofuranoside

Base Information

• Chemical Name: Methyl 3,5-di-O-benzyl-D-ribofuranoside
• CAS No.: 55775-39-8
• Molecular Formula: C20H24O5
• Molecular Weight: 344.40156
• Mol file: 55775-39-8.mol

Synonyms:methyl 3,4-di-O-benzyl-D-ribofuranoside;Methyl 3,5-di-O-benzyl-D-ribofuranoside;3,5-di-O-benzyl-1-O-methyl-D-ribofuranose;

Chemical Property of Methyl 3,5-di-O-benzyl-D-ribofuranoside

Chemical Property:

• Boiling Point: 497.0±45.0 °C(Predicted)
• PKA: 13.01±0.70(Predicted)
• PSA: 57.15000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 2.52080

Purity/Quality:

97% ^*data from raw suppliers

(3R,4S,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Methyl 3,5-di-O-benzyl-D-ribofuranoside

There total 9 articles about Methyl 3,5-di-O-benzyl-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: 89.0%

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose (55735-86-9) + acetyl chloride (75-36-5) → 1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside (55775-39-8)

Guidance literature:

In methanol; at 20 ℃;

DOI:10.1016/j.bmcl.2011.01.042

Reference yield:

D-xylofuranose (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-O-methyl-3,5-di-O-benzyl-D-ribofuranoside (55775-39-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sulfuric acid / water / 0.5 h / 20 °C

1.2: 0 - 20 °C

2.1: triethylamine / dichloromethane / 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / -80 °C / Inert atmosphere

3.2: 3.67 h / -80 - 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / ethanol; water / 4 h / 0 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran

6.1: sodium hydride / tetrahydrofuran / -20 - 20 °C / Inert atmosphere

6.2: 3 h / 20 °C / Inert atmosphere

7.1: methanol / 20 °C

With sodium tetrahydroborate; oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 3.1: Swern oxidation / 3.2: Swern oxidation;

DOI:10.1016/j.bmcl.2011.01.042

Reference yield:

1,2-isopropylidene-α-D-ribofuranose (37077-81-9) → 1-O-methyl-3,5-di-O-benzyl-D-ribofuranoside (55775-39-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / -20 - 20 °C / Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: methanol / 20 °C

With sodium hydride; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2011.01.042

upstream raw materials:

3,5-O-dibenzyloxy-1,2-O-isorpopylidene-α-D-ribofuranose

D-xylofuranose

1,2-isopropylidene-α-D-ribofuranose

benzyl bromide

Downstream raw materials:

Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-β-D-ribofuranoside

Methyl 3,5-Di-O-benzyl-2-O-(trifluoromethanesulfonyl)-α-D-ribofuranoside

1,4-anhydro-3,5-di-O-benzyl-D-ribitol

3,5-di-O-benzyl-1-O-methyl-β-D-[2-2H1]arabinofuranose