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

Base Information

• Chemical Name: (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran
• CAS No.: 116490-72-3
• Molecular Formula: C₂₃H₂₈O₅
• Molecular Weight: 384.472
• Mol file: 116490-72-3.mol

Synonyms:(2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran

Chemical Property of (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran

There total 5 articles about (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran 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: 80.0%

benzyl bromide (100-39-0) + (2R,3S,4R,5R)-2-(allyloxymethyl)-5-methoxytetrahydrofuran-3,4-diol → (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran (116490-72-3)

Guidance literature:

(2R,3S,4R,5R)-2-(allyloxymethyl)-5-methoxytetrahydrofuran-3,4-diol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.tetlet.2018.07.052

Reference yield: 58.0%

benzyl bromide (100-39-0) + methyl 5-O-allyl-D-ribofuranoside (116490-68-7,116490-69-8,128775-32-6) → (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran (116490-72-3) + Methyl 5-O-allyl-2,3-di-O-benzyl-α-D-ribofuranoside (116490-73-4)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/0008-6215(88)84144-2

Reference yield:

benzyl chloride (100-44-7) + (2R,3S,4R,5R)-2-(allyloxymethyl)-5-methoxytetrahydrofuran-3,4-diol → (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran (116490-72-3)

Guidance literature:

(2R,3S,4R,5R)-2-(allyloxymethyl)-5-methoxytetrahydrofuran-3,4-diol; With sodium hydride; In DMF (N,N-dimethyl-formamide); at 0 ℃; for 0.5h;

benzyl chloride; In DMF (N,N-dimethyl-formamide); for 2h;

upstream raw materials:

benzyl bromide

methyl 5-O-allyl-D-ribofuranoside

β-5-O-allyl-1-O-methyl-2,3-O,O-isopropylidene-D-ribofuranoside

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Downstream raw materials:

5-O-allyl-2,3-di-O-benzyl-β-D-ribofuranose

5-O-allyl-1,2,3-tri-O-benzyl-D-ribitol

5-O-allyl-2,3-di-O-benzyl-D-ribitol

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol