Methyl 3,5-di-O-benzyl-D-xylofuranoside

Base Information

• Chemical Name: Methyl 3,5-di-O-benzyl-D-xylofuranoside
• CAS No.: 132487-16-2
• Molecular Formula: C20H24O4
• Molecular Weight: 328.408
• DSSTox Substance ID: DTXSID90452352
• Mol file: 132487-16-2.mol

Synonyms:Methyl 3,5-di-O-benzyl-D-xylofuranoside;(3R,4R,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol;(3R,4R,5R)-4-(Benzyloxy)-5-((benzyloxy)methyl)-2-methoxytetrahydrofuran-3-ol;DTXSID90452352;102339-30-0;METHYL-3,5-DI-O-BENZYL-D-THREO-PENTAFURANOSIDE

Chemical Property of Methyl 3,5-di-O-benzyl-D-xylofuranoside

Chemical Property:

• PSA: 36.92000
• LogP: 3.55000
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 344.16237386
• Heavy Atom Count: 25
• Complexity: 365

Purity/Quality:

97% ^*data from raw suppliers

Methyl3-5-di-O-benzyl-D-xylofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)O
• Isomeric SMILES: COC1[C@@H]([C@H]([C@H](O1)COCC2=CC=CC=C2)OCC3=CC=CC=C3)O

Technology Process of Methyl 3,5-di-O-benzyl-D-xylofuranoside

There total 5 articles about Methyl 3,5-di-O-benzyl-D-xylofuranoside 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: 92.0%

benzyl bromide (100-39-0) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2)

Guidance literature:

1-O-methyl-2-deoxy-D-ribofuranoside; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 1h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃;

DOI:10.1039/c6ob01199c

Reference yield: 87.0%

benzyl chloride (100-44-7) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; for 24h; Heating;

DOI:10.1021/ol701794u

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / HCl, Ag₂CO₃ / 0 °C

2: 87 percent / NaH, n-Bu₄NI / tetrahydrofuran / Ambient temperature

With hydrogenchloride; tetra-(n-butyl)ammonium iodide; sodium hydride; silver carbonate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(99)00854-0

upstream raw materials:

benzyl bromide

1-O-methyl-2-deoxy-D-ribofuranoside

benzyl chloride

D-2-deoxyribose

Downstream raw materials:

3,5-di-O-benzyl-2-deoxy-D-ribofuranose

Phenyl 3,5-di-O-benzyl-2-deoxy-1-seleno-D-ribofuranoside

(2R,3S)-3-(benzyloxy)-2-(benzyloxymethyl)-5-(phenylthio)tetrahydrofuran

3,4-di-O-benzyl-2-deoxy-D-erythro-pentose bisbenzyl dithioacetal