methyl 2,3,4-tri-O-benzoylpentopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzoylpentopyranoside
• CAS No.: 6638-76-2
• Molecular Formula: C27H24 O8
• Molecular Weight: 476.4747
• Mol file: 6638-76-2.mol

Synonyms:Xylopyranoside,methyl, tribenzoate (7CI); Xylopyranoside, methyl, tribenzoate, b-D- (8CI); NSC 48285

Chemical Property of methyl 2,3,4-tri-O-benzoylpentopyranoside

Chemical Property:

• Vapor Pressure: 5.39E-15mmHg at 25°C
• Boiling Point: 613.7°C at 760 mmHg
• Flash Point: 262.5°C
• Density: 1.32g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 2,3,4-tri-O-benzoylpentopyranoside

There total 28 articles about methyl 2,3,4-tri-O-benzoylpentopyranoside 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: 43.0%

benzoyl chloride (98-88-4) + methyl-β-D-xylopyranoside (612-05-5) → 1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside (6638-76-2)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; Cooling with ice;

DOI:10.1021/jm8008713

Reference yield: 22.0%

benzoyl chloride (98-88-4) + methyl-β-D-xylopyranoside (612-05-5) → methyl 2,4-di-O-benzoyl-β-D-xylopyranoside (83158-26-3) + methyl 2,3-di-O-benzoyl-β-D-xylopyranoside (83158-27-4) + methyl 3,4-di-O-benzoyl-β-D-xylopyranoside (83158-28-5) + 1-O-methyl-2,3,4-O-tri-benzoyl-β-D-xylopyranoside (6638-76-2)

Guidance literature:

In pyridine; at 0 - 25 ℃; for 96h; Further byproducts given; 2 molar equivalents of benzoyl chloride;

DOI:10.1016/S0008-6215(00)80551-0

Reference yield:

1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → methyl tri-O-benzoyl-α-D-arabinopyranoside (6638-76-2,10225-75-9,10225-76-0,10225-77-1,10225-78-2,13035-45-5,32445-39-9,33640-74-3,88165-09-7,88165-10-0,145306-49-6)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine

2: sodium methylate; methanol; dichloromethane

3: pyridine

With pyridine; methanol; dichloromethane; sodium methylate;

DOI:10.1021/ja01599a048

upstream raw materials:

benzoyl chloride

(2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol

methanol

2,3,4-tri-O-benzoyl-β-D-arabinopyranosyl bromide

Downstream raw materials:

(2S,3S,4R,5R)-2-Methoxy-tetrahydro-pyran-3,4,5-triol

methyl β-D-ribopyranoside

methyl 3,4-O-isopropylidene-2-O-methanesulfonyl-α-D-arabinopyranoside

methyl 2-O-methanesulfonyl-α-D-arabinopyranoside

Refernces

• 1、 Putra, Masteria Yunovilsa,Ianaro, Angela,Panza, Elisabetta,Bavestrello, Giorgio,Cerrano, Carlo,Fattorusso, Ernesto,Taglialatela-Scafati, Orazio. "Sinularioside, a triacetylated glycolipid from the Indonesian soft coral Sinularia sp., is an inhibitor of NO release". body text. p. 2723 - 2725. Retrieved 2012/06/01.
• 2、 Costantino, Valeria,Fattorusso, Ernesto,Imperatore, Concetta,Mangoni, Alfonso. "Vesparioside from the marine sponge Spheciospongia vesparia, the first diglycosylceramide with a pentose sugar residue". . p. 368 - 373. Retrieved 2007/10/03.