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

Base Information

• Chemical Name: (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran
• CAS No.: 89824-86-2
• Molecular Formula: C₂₇H₃₀O₅
• Molecular Weight: 434.532
• Mol file: 89824-86-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 29 articles about (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-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: 100.0%

benzyl bromide (100-39-0) + methyl 3,5-di-O-benzyl-α-D-ribofuranoside (191543-71-2) → methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside (64363-77-5,79083-29-7,79083-32-2,79083-33-3,79083-40-2,79083-41-3,79083-43-5,79083-44-6,85549-73-1,85610-74-8,89824-86-2,131615-65-1,131896-99-6,135910-14-4,135911-60-3,55725-85-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1246/bcsj.74.1679

Reference yield: 98.0%

2,3,5-tri-O-benzyl-D-ribofuranose (16838-89-4) + Trimethylmethoxysilane (1825-61-2) → methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside (64363-77-5,79083-29-7,79083-32-2,79083-33-3,79083-40-2,79083-41-3,79083-43-5,79083-44-6,85549-73-1,85610-74-8,89824-86-2,131615-65-1,131896-99-6,135910-14-4,135911-60-3,55725-85-4)

Guidance literature:

With trifluoromethylsulfonic anhydride; diphenyltin sulfide; cesium fluoride; In diethyl ether;

Reference yield: 95.0%

benzyl bromide (100-39-0) + methyl D-arabinofuranoside (79083-42-4) → (2R,3R,4S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran (89824-86-2)

Guidance literature:

methyl D-arabinofuranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1055/s-0028-1087343

upstream raw materials:

methanol

2,3,5-tris-O-(phenylmethyl)-β-D-ribofuranosyl fluoride

2,3,5-tri-O-benzyl-D-ribofuranose

methyl phosphite

Downstream raw materials:

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

(2R,3R,4S)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol

1,4-anhydro-D-ribitol

(2R,3R,4R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-phenylsulfanyl-tetrahydro-furan