methyl 6-O-[(4-methylphenyl)sulfonyl]-alpha-D-galactopyranoside

Base Information

• Chemical Name: methyl 6-O-[(4-methylphenyl)sulfonyl]-alpha-D-galactopyranoside
• CAS No.: 6619-09-6
• Molecular Formula: C14H20O8S
• Molecular Weight: 348.374
• NSC Number: 170172
• DSSTox Substance ID: DTXSID70305312
• Mol file: 6619-09-6.mol

Synonyms:methyl 6-O-[(4-methylphenyl)sulfonyl]-alpha-D-galactopyranoside;(3,4,5-trihydroxy-6-methoxyoxan-2-yl)methyl 4-methylbenzenesulfonate;6619-09-6;methyl 6-o-tosyl-alpha-d-glucopyranoside;Methyl 6-O-tosyl-a-D-glucopyranoside;NSC170172;SCHEMBL17099845;DTXSID70305312;AKOS024331771;NSC-170172;FT-0636194;Methyl 6-O-(4-methylbenzene-1-sulfonyl)hexopyranoside

Chemical Property of methyl 6-O-[(4-methylphenyl)sulfonyl]-alpha-D-galactopyranoside

Chemical Property:

• Vapor Pressure: 6.15E-13mmHg at 25°C
• Melting Point: 123-125 °C
• Boiling Point: 550.2°Cat760mmHg
• PKA: 12.81±0.70(Predicted)
• Flash Point: 286.5°C
• PSA: 130.90000
• Density: 1.47g/cm³
• LogP: 0.23510
• Storage Temp.: 2-8°C
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 348.08788877
• Heavy Atom Count: 23
• Complexity: 468

Purity/Quality:

99% ^*data from raw suppliers

Methylα-?D-?Glucopyranoside6-?(4-?Methylbenzenesulfona?te) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2C(C(C(C(O2)OC)O)O)O
• Uses: Methyl α-?D-?Glucopyranoside 6-?(4-?Methylbenzenesulfona?te) is an intermediate in synthesizing Ranimustine (R120030), a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia and polycythemia vera. It can be used in biological study of synthesis of anti-EGFR antibody-drug conjugates. It can also be used in therapeutic use and biological study of BCMA (B-Cell Maturation Antigen) antigen binding proteins.

Technology Process of methyl 6-O-[(4-methylphenyl)sulfonyl]-alpha-D-galactopyranoside

There total 14 articles about methyl 6-O-[(4-methylphenyl)sulfonyl]-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: 76.0%

p-toluenesulfonyl chloride (98-59-9) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 6-O-tosyl-α-D-glucopyranoside (6619-09-6)

Guidance literature:

With pyridine; at 0 ℃; for 16h;

DOI:10.1002/anie.201603921

Reference yield: 9.0%

N-tosylimidazole (2232-08-8) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 6-O-tosyl-α-D-glucopyranoside (6619-09-6)

Guidance literature:

N-tosylimidazole; methyl-alpha-D-glucopyranoside; In neat (no solvent, solid phase); for 0.0833333h; Milling;

With potassium hydroxide; In neat (no solvent, solid phase); for 0.0833333h; Milling;

DOI:10.1021/acs.joc.5b00697

Reference yield: 2.7%

p-toluenesulfonyl chloride (98-59-9) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 2,6-bis-α-D-glucopyranoside (54497-89-1) + methyl 6-O-tosyl-α-D-glucopyranoside (6619-09-6) + methyl 2-O-(4-toluene)sulfonyl-α-D-glucopyranoside (5596-21-4)

Guidance literature:

With pyridine; for 48h; Ambient temperature;

DOI:10.1515/znb-1996-0622

upstream raw materials:

methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside

methyl-[O²,O³,O⁴-tribenzoyl-O⁶-(toluene-4-sulfonyl)-α-D-glucopyranoside]

p-toluenesulfonyl chloride

methyl-alpha-D-glucopyranoside

Downstream raw materials:

6-azido-6-deoxy-2,3,4-tri-O-benzyl-N-(prop-2-yn-1-yl)-D-gluconamide

6-azido-2,3,4-tri-O-benzyl-6-deoxy-D-glucono-1,5-lactone

((2R,3R,4S,5R,6S)-3,4,5,6-tetramethoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate

methyl-[O²,O³,O⁴-tribenzoyl-O⁶-(toluene-4-sulfonyl)-α-D-glucopyranoside]

Refernces

• 1、 Proietti, Giampiero,Prathap, Kaniraj Jeya,Ye, Xinchen,Olsson, Richard T.,Dinér, Peter. "Nickel Boride Catalyzed Reductions of Nitro Compounds and Azides: Nanocellulose-Supported Catalysts in Tandem Reactions". supporting information. p. 133 - 146. Retrieved 2021/11/04.
• 2、 Dong, Hai,Liu, Yu,Lv, Jian,Zhu, Jia-Jia. "Regioselective Sulfonylation/Acylation of Carbohydrates Catalyzed by FeCl3 Combined with Benzoyltrifluoroacetone and Its Mechanism Study". . p. 3307 - 3319. Retrieved 2020/03/25.