Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside

Base Information

• Chemical Name: Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside
• CAS No.: 3601-36-3
• Molecular Formula: C28H26O9
• Molecular Weight: 506.509
• Hs Code.: 29329990
• European Community (EC) Number: 609-199-4
• DSSTox Substance ID: DTXSID80448643
• Nikkaji Number: J1.516.320H
• Wikidata: Q72491038
• Mol file: 3601-36-3.mol

Synonyms:3601-36-3;Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside;(2S,3R,4S,5S,6R)-6-((benzoyloxy)methyl)-5-hydroxy-2-methoxytetrahydro-2H-pyran-3,4-diyl dibenzoate;Methyl 2,3,6-tri-O-benzoyl-|A-D-galactopyranoside;Methyl 2,3,6-tri-O-benzoyl-a-D-galactopyranoside;[(2R,3S,4S,5R,6S)-4,5-dibenzoyloxy-3-hydroxy-6-methoxyoxan-2-yl]methyl benzoate;Methyl D-galactopyranoside 2,3,6-tribenzoate;SCHEMBL1682180;DTXSID80448643;AMY24693;MFCD06200842;HY-W145595;AS-74683;CS-0226021;D91556;A874464;Methyl 2,3,6-Tri-O-benzoyl-?-D-galactopyranoside;W-202494;Methyl 2,3,6-Tri-O-benzoyl- alpha -D-galactopyranoside;Methyl 2-O,3-O,6-O-tribenzoyl-alpha-D-galactopyranoside;(2S,3R,4S,5S,6R)-6-(benzoyloxymethyl)-5-hydroxy-2-methoxytetrahydro-2H-pyran-3,4-diyl dibenzoate;[(2R,3S,4S,5R,6S)-4,5-BIS(BENZOYLOXY)-3-HYDROXY-6-METHOXYOXAN-2-YL]METHYL BENZOATE

Chemical Property of Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside

Chemical Property:

• Appearance/Colour: White crystalline solid
• Melting Point: 143 °C
• Refractive Index: 123 ° (C=1, CHCl3)
• Boiling Point: 666.202 °C at 760 mmHg
• Flash Point: 220.273 °C
• PSA: 117.59000
• Density: 1.352 g/cm³
• LogP: 3.02680
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ether, Ethyl Acetate, Methanol
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 506.15768240
• Heavy Atom Count: 37
• Complexity: 753

Purity/Quality:

99% ^*data from raw suppliers

Methyl 2,3,6-tri-O-benzoyl-a-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(C(C(O1)COC(=O)C2=CC=CC=C2)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)COC(=O)C2=CC=CC=C2)O)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Uses: Methyl 2,3,6-Tri-O-benzoyl-α-D-galactopyranoside (cas# 3601-36-3) is a compound useful in organic synthesis.

Technology Process of Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside

There total 15 articles about Methyl 2,3,6-Tri-O-benzoyl-alpha-D-galactopyranoside 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: 80.0%

methyl 2,3,6-tri-O-benzoyl-4-O-(tert-butyl)dimethylsilyl-α-D-galactopyranoside → methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside (3601-36-3,6344-46-3)

Guidance literature:

With SO₃H silica gel; In n-heptane; at 20 ℃; for 70h;

DOI:10.1016/j.tet.2017.07.047

Reference yield: 80.0%

C37H46O9Si (356060-80-5,356060-82-7) → methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside (3601-36-3,6344-46-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0040-4039(01)00611-6

Reference yield: 76.0%

benzoyl chloride (98-88-4) + methyl α-D-galactopyranoside (3396-99-4) → methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside (3601-36-3,6344-46-3)

Guidance literature:

With pyridine; at 9 - 18 ℃; Large scale reaction;

DOI:10.1021/op100053k

upstream raw materials:

benzoyl chloride

methyl α-D-galactopyranoside

methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-galactopyranoside

C₃₇H₄₆O₉Si

Downstream raw materials:

methyl 2,3,6-tri-O-benzoyl-4-O-benzyl-α-D-galactopyranoside

methyl 2,3,6-tri-O-benzoyl-4-O-methylsulphonyl-α-D-galactopyranoside

methyl 2,3,6-tri-benzoyl-4-O-(bromoacetyl)-α-D-galactopyranoside

Methyl-2,3,6-tri-O-benzoyl-4-O-phenoxythiocarbonyl-α-D-galactopyranosid

Refernces

• 1、 -. "Total synthesis method for xinaomycin". Paragraph 0033; 0065; 0067; 0068. . Retrieved 2018/05/16.
• 2、 Lei, Zhiwei,Wang, Jie,Mao, Genlin,Wen, Yingjie,Tian, Yuxin,Wu, Huawei,Li, Yufeng,Xu, Hanhong. "Glucose positions affect the phloem mobility of glucose-fipronil conjugates". . p. 6065 - 6071. Retrieved 2014/07/21.