(2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran
• CAS No.: 326586-21-4
• Molecular Formula: C₂₉H₃₂O₄
• Molecular Weight: 444.571
• Mol file: 326586-21-4.mol

Synonyms:(2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran

Chemical Property of (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran

There total 4 articles about (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran 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: 77.0%

(2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran (89824-86-2) + allyl-trimethyl-silane (762-72-1) → (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran (326586-21-4)

Guidance literature:

With [ReOCl₃(OPPh₃)(SMe₂)]; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at -50 - -30 ℃; for 12h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.joc.1c00706

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranosyl ortho-hexynylbenzoate + allyl-trimethyl-silane (762-72-1) → 1-allyl-3,4,5-tri-O-benzyl-1-deoxy-β-D-arabinofuranose (326586-22-5) + (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran (326586-21-4)

Guidance literature:

2,3,5-tri-O-benzyl-D-arabinofuranosyl ortho-hexynylbenzoate; allyl-trimethyl-silane; In dichloromethane; at 20 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I); In dichloromethane; at 20 ℃; for 0.5h; Overall yield = 87 %; Overall yield = 77 mg; Molecular sieve; Inert atmosphere;

DOI:10.1039/c6cc07218f

Reference yield:

benzyl bromide (100-39-0) + methyl D-arabinofuranoside (79083-42-4) → (2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-tetrahydrofuran (326586-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: [ReOCl₃(OPPh₃)(SMe₂)]; copper(II) bis(trifluoromethanesulfonate) / dichloromethane / 12 h / -50 - -30 °C / Inert atmosphere

With [ReOCl₃(OPPh₃)(SMe₂)]; copper(II) bis(trifluoromethanesulfonate); sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/acs.joc.1c00706

upstream raw materials:

2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride

allylmagnesium bromide

allyl-trimethyl-silane

(2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran