pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside

Base Information

• Chemical Name: pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside
• CAS No.: 205485-59-2
• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.499
• Mol file: 205485-59-2.mol

Synonyms:pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside

Chemical Property of pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside

There total 13 articles about pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside 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:

C24H28O5 (1431370-71-6) → pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside (205485-59-2)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/ol400931p

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) + (3aS,5R,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole (131139-02-1) → pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside (205485-59-2) + 4-pentenyl 3,5-di-O-benzyl-α-D-arabinofuranoside (205485-60-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 60 ℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1039/a707796c

Reference yield:

benzyl bromide (100-39-0) → pent-4-enyl 3,5-di-O-benzyl-β-D-arabinofuranoside (205485-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / NaH / dimethylformamide / 0 - 20 °C

2: TsOH / CH₂Cl₂ / 2 h / 60 °C

With sodium hydride; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/a707796c

upstream raw materials:

n-Pent-4-enyl alcohol

(3aS,5R,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

benzyl bromide

1,2-O-isopropylidene-β-D-arabinofuranoside

Downstream raw materials:

4-pentenyl 2-O-[2,3,5-tri-O-benzyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-β-D-arabinofuranoside

{(3aS,5R,6R,6aS)-6-[(2R,3S,4R,5R)-4-Benzyloxy-5-benzyloxymethyl-3-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-furan-2-yloxy]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl}-methanol

Refernces

• 1、 Mereyala, Hari Babu,Hotha, Srinivas,Gurjar, Mukund K.. "Synthesis of pentaarabinofuranosyl structure motif A of Mycobacterium tuberculosis". . p. 685 - 686. Retrieved 2007/10/03.