3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose

Base Information

• Chemical Name: 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose
• CAS No.: 93215-31-7
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.284
• Mol file: 93215-31-7.mol

Synonyms:

Chemical Property of 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose

There total 8 articles about 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose 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:

5-deoxy-5-iodo-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylofuranose (29873-56-1) → 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose (93215-31-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / hydrogen / 10 percent Pd/C / ethanol / 25 °C

2: 93 percent / acetic acid, conc. sulfuric acid / 16 h / 20 °C

3: 45 percent / hydrochloric acid / 16 h / 20 °C

4: 85 percent / sodium / methanol / 96 h / 5 °C

5: 1.) copper(I) iodide / 1.) ether, 2.) ether, 0 deg C

6: 83 percent / calcium sulfate, 85 percent potassium hydroxide / various solvent(s) / 26 h / Heating

7: trifluoroacetic acid, water / acetonitrile / 1.) 30 min, 0 deg C, 2.) 22 h, 20 deg C

With hydrogenchloride; calcium sulfate; potassium hydroxide; copper(l) iodide; sulfuric acid; water; hydrogen; sodium; acetic acid; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; acetonitrile;

DOI:10.1016/0008-6215(84)85225-8

Reference yield:

methyl 2,3-anhydro-5-deoxy-α-D-ribofuranoside (52630-69-0) → 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose (93215-31-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) copper(I) iodide / 1.) ether, 2.) ether, 0 deg C

2: 83 percent / calcium sulfate, 85 percent potassium hydroxide / various solvent(s) / 26 h / Heating

3: trifluoroacetic acid, water / acetonitrile / 1.) 30 min, 0 deg C, 2.) 22 h, 20 deg C

With calcium sulfate; potassium hydroxide; copper(l) iodide; water; trifluoroacetic acid; In acetonitrile;

DOI:10.1016/0008-6215(84)85225-8

Reference yield:

O1,O2-isopropylidene-O3-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose (16713-89-6) → 3-O-benzyl-2,5-dideoxy-2-C-methyl-α-D-arabinofuranose (93215-31-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / acetic acid, conc. sulfuric acid / 16 h / 20 °C

2: 45 percent / hydrochloric acid / 16 h / 20 °C

3: 85 percent / sodium / methanol / 96 h / 5 °C

4: 1.) copper(I) iodide / 1.) ether, 2.) ether, 0 deg C

5: 83 percent / calcium sulfate, 85 percent potassium hydroxide / various solvent(s) / 26 h / Heating

6: trifluoroacetic acid, water / acetonitrile / 1.) 30 min, 0 deg C, 2.) 22 h, 20 deg C

With hydrogenchloride; calcium sulfate; potassium hydroxide; copper(l) iodide; sulfuric acid; water; sodium; acetic acid; trifluoroacetic acid; In methanol; acetonitrile;

DOI:10.1016/0008-6215(84)85225-8

upstream raw materials:

methyl-2,5-didesoxy-2-C-methyl-3-O-benzyl-α-D-arabinofuranoside

methyl 2,3-anhydro-5-deoxy-α-D-ribofuranoside

5-deoxy-5-iodo-1,2-O-isopropylidene-3-O-p-tolylsulfonyl-α-D-xylofuranose

O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose

Downstream raw materials:

4-O-acetyl-3-O-benzyl-2,5-dideoxy-2-C-methyl-D-arabinose diethyl dithioacetal

4-O-acetyl-3-O-benzyl-2,5-dideoxy-2-C-methyl-D-arabinose dimethyl acetal