methyl beta-D-mannopyranoside

Base Information

• Chemical Name: methyl beta-D-mannopyranoside
• CAS No.: 22277-65-2
• Molecular Formula: C7H14 O6
• Molecular Weight: 194.185
• ChEMBL ID: CHEMBL4117365
• Metabolomics Workbench ID: 55652
• Nikkaji Number: J377.963G
• Wikidata: Q27117219
• Mol file: 22277-65-2.mol

Synonyms:alpha-methyl-D-mannose;alpha-methylmannose;alpha-methylmannoside;beta-methylmannoside;methyl alpha-D-mannopyranoside;methyl beta-D-mannopyranoside;methyl D-mannopyranoside;methyl mannoside;methyl mannoside, (alpha-D)-isomer;methyl-alpha-D-mannoside;methylmannose;methylmannoside;methylmannoside, alpha-D-isomer

Chemical Property of methyl beta-D-mannopyranoside

Chemical Property:

• PSA: 99.38000
• LogP: -2.56730
• Storage Temp.: 2-8°C
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 194.07903816
• Heavy Atom Count: 13
• Complexity: 163

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: CO[C@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

Technology Process of methyl beta-D-mannopyranoside

There total 211 articles about methyl beta-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: 99.0%

tert-Butyl-diphenyl-((2R,3R,4S,5R)-3,4,5-tris-benzyloxymethoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-silane → methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6)

Guidance literature:

With methanol; bromine; for 0.333333h; Heating;

DOI:10.1055/s-2001-15136

Reference yield: 90.0%

methanol (67-56-1) + D-glucose ethylene dithioacetal (3650-65-5) → methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6)

Guidance literature:

With iodine; for 18h; Heating;

DOI:10.1016/S0040-4039(00)83890-3

Reference yield:

methanol (67-56-1) + D-Mannose (530-26-7) → Methyl mannoside (22277-65-2) + (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9)

Guidance literature:

With hydrogenchloride; for 16h; Heating;

DOI:10.1016/0008-6215(83)88042-2

upstream raw materials:

methanol

D-Mannose

sodium methylate

water

Downstream raw materials:

methyl exo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside

methyl endo-2,3:4,6-di-O-benzylidene-β-D-mannopyranoside

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

methyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside

Refernces

• 1、 Chen, Kuanwei,Xie, Tao,Shen, Yanfang,He, Haibing,Zhao, Xiaoli,Gao, Shuanhu. "Calixanthomycin A: Asymmetric Total Synthesis and Structural Determination". supporting information. p. 1769 - 1774. Retrieved 2021/03/08.
• 2、 Bertella, Anis,Bitam, Fatma,Carbone, Marianna,Ciavatta, Maria Letizia,Gavagnin, Margherita,Smadi, Abla. "Chemical constituents of the aerial parts of Algerian Galium brunneum: Isolation of new hydroperoxy sterol glucosyl derivatives". . p. 39 - 45. Retrieved 2020/05/25.