Benzyl alpha-D-mannopyranoside

Base Information

• Chemical Name: Benzyl alpha-D-mannopyranoside
• CAS No.: 15548-45-5
• Molecular Formula: C13H18 O6
• Molecular Weight: 270.282
• Hs Code.: 29389090
• ChEMBL ID: CHEMBL1170453
• Metabolomics Workbench ID: 122519
• Nikkaji Number: J81.875E
• Mol file: 15548-45-5.mol

Synonyms:Benzyl alpha-D-mannopyranoside;Benzyl a-D-mannopyranoside;15548-45-5;MFCD00153924;(2S,3S,4S,5S,6R)-2-(Benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;CHEMBL1170453;SCHEMBL117781;Benzyl alpha -D-mannopyranoside;(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-phenylmethoxyoxane-3,4,5-triol;AKOS015900487;Benzyl alpha-D-mannopyranoside, >=98%;E88149;A809648;W-201404

Chemical Property of Benzyl alpha-D-mannopyranoside

Chemical Property:

• Appearance/Colour: White Crystalline Solid
• Melting Point: 126-129°C
• Refractive Index: 1.612
• Boiling Point: 480.2±45.0 °C(Predicted)
• PKA: 12.93±0.70(Predicted)
• PSA: 99.38000
• Density: 1.40±0.1 g/cm3(Predicted)
• LogP: -0.99690
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 270.11033829
• Heavy Atom Count: 19
• Complexity: 268

Purity/Quality:

98% ^*data from raw suppliers

Benzyl a-D-Mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)CO[C@@H]2[C@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of Benzyl alpha-D-mannopyranoside

There total 41 articles about Benzyl alpha-D-mannopyranoside 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 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (10343-13-2,30657-70-6,31281-76-2,53729-76-3,142696-63-7,83113-54-6) → benzyl β-D-galactopyranoside (4304-12-5,14897-46-2,15548-45-5,25320-99-4,34246-23-6,47000-20-4,53448-50-3,86196-36-3,133908-86-8)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1246/cl.1995.39

Reference yield: 98.0%

D-Mannose (530-26-7) + benzyl alcohol (100-51-6,185532-71-2) → (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (15548-45-5)

Guidance literature:

With acetyl chloride; at 20 - 50 ℃; for 16.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.01.064

Reference yield: 95.0%

O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (10343-13-2,30657-70-6,31281-76-2,83113-54-6,142696-63-7,53729-76-3) → (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol (15548-45-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/ejoc.200801024

upstream raw materials:

benzyl alcohol

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Benzyl 3,4-O-isopropylidene-β-D-galactopyranoside

benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

Downstream raw materials:

Benzyl 4,6-O-isopropylidene-α-D-mannopyranoside

(2S,3S,4R,4aS,10aR)-2-Benzyloxy-6,6,8,8-tetraisopropyl-hexahydro-1,5,7,9-tetraoxa-6,8-disila-benzocyclooctene-3,4-diol

benzyl exo-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

benzyl endo-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

Refernces

• 1、 Dey, Kalyan,Jayaraman, Narayanaswamy. "Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions". supporting information. p. 2224 - 2227. Retrieved 2022/02/17.
• 2、 Li, MaoLin,Huang, Weiping,Jiang, Zhilin,Shi, Yonghui,Yuan, Sisi,Fu, Kaishuo,Chen, YongJun,Zhou, Li,Zhou, Wen. "Multi-gram scale synthesis of a bleomycin (BLM) carbohydrate moiety: exploring the antitumor beneficial effect of BLM disaccharide attached to 10-hydroxycamptothecine (10-HCPT)". . p. 6010 - 6020. Retrieved 2019/04/17.