6619-09-6

Basic information

• Product Name: METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE;methyl 6-O-((4-methylphenyl)sulfonyl)-alpha-D-galactopyranoside;Methyl 6-O-tosyl-alpha-D-galactopyranoside;Methyl 6-O-(4-methylphenyl)sulfonyl-α-D-glucopyranoside;Methyl 6-O-Tosyl-α-D-glucopyranoside;Methyl 6-O-tosyl-a-D-glucopyranoside
• CAS NO: 6619-09-6
• Molecular Formula: C₁₄H₂₀O₈S
• Molecular Weight: 348.37
• Mol File: 6619-09-6.mol
• Article Data: 26

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 550.2°Cat760mmHg
• Flash Point: 286.5°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 6.15E-13mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: 2-8°C
• PKA: 12.81±0.70(Predicted)
• CAS DataBase Reference: METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE(6619-09-6)
• EPA Substance Registry System: METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE(6619-09-6)

Safety Data

• Hazardous Substances Data: 6619-09-6(Hazardous Substances Data)

Usage

Description

METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE is a chemical compound that serves as an intermediate in the synthesis of various pharmaceutical agents and is utilized in biological studies and therapeutic applications.

Uses

Used in Pharmaceutical Synthesis:
METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE is used as an intermediate in the synthesis of Ranimustine (R120030), a nitrosourea alkylating agent approved in Japan for the treatment of chronic myelogenous leukemia and polycythemia vera.
Used in Biological Studies:
METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE is used as a research compound for studying the synthesis of anti-EGFR antibody-drug conjugates, which have potential applications in targeted cancer therapies.
Used in Therapeutic Applications:
METHYL 6-O-TOSYL-ALPHA-D-GLUCOPYRANOSIDE is used in the therapeutic use and biological study of BCMA (B-Cell Maturation Antigen) antigen binding proteins, which are being explored for their potential in treating certain types of cancer, particularly multiple myeloma.

InChI:InChI=1/C14H20O8S/c1-8-3-5-9(6-4-8)23(18,19)21-7-10-11(15)12(16)13(17)14(20-2)22-10/h3-6,10-17H,7H2,1-2H3

Upstream product

• 2232-08-8 N-tosylimidazole 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 
• 20231-39-4 methyl 2,3,4-tri-O-benzoyl-6-O-triphenylmethyl-α-D-glucopyranoside 
• 98-59-9 p-toluenesulfonyl chloride 
• 34234-44-1 methyl 2,3,4-tri-O-benzoylglucopyranoside 
• 67-56-1 methanol 
• 7664-41-7 ammonia 
• 1153940-62-5 methyl-[O²,O³,O⁴-tribenzoyl-O⁶-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 23397-70-8 methyl 2,3-di-O-benzoyl-4,6-di-O-tosyl-α-D-glucopyranoside 
• 23661-33-8 methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside 

Downstream Products

• 23701-87-3 methyl 6-azido-6-deoxy-α-D-glucopyranoside 
• 494804-64-7 C₁₄H₂₀O₅S 
• 5155-47-5 methyl 6-amino-6-deoxy-α-D-glucopyranoside 
• 57467-09-1 ((2R,3R,4S,5R,6S)-3,4,5,6-tetramethoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate 
• 1153940-62-5 methyl-[O²,O³,O⁴-tribenzoyl-O⁶-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 95118-61-9 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α,β-D-glucopyranose 
• 88713-76-2 6-azido-2,3,4-tri-O-benzyl-6-deoxy-D-glucono-1,5-lactone 
• 1582309-47-4 6-azido-6-deoxy-2,3,4-tri-O-benzyl-N-(prop-2-yn-1-yl)-D-gluconamide 
• 19139-89-0 (2R,3R,4S,5R,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 

Relevant articles and documents

Selective Secondary Face Modification of Cyclodextrins by Mechanosynthesis

α-, β-, and γ-cyclodextrins (CDs) were modified on their secondary face by mechanosynthesis at room temperature using a laboratory-scale ball-mill. Mono-2-tosylated α-, β-, and γ-CDs were obtained in good yield from mixtures of native α-, β-, and γ-CDs, r

TBAF Effects 3,6-Anhydro Formation from 6-O-Tosyl Pyranosides

3,6-Anhydro sugars are common structures in algal polysaccharides and occur in the furanodictine and sauropunol natural products. We have found that treatment of 6-O-tosylpyranosides with tetrabutylammonium fluoride provides a mild, high-yielding synthesis of 3,6-anhydro sugars. Using O-glycoside substrates, 3,6-anhydropyranosides are isolated and the use of N,O-dimethyl hydroxylamine glycosides yields 3,6-anhydrofuranosides. Applying this approach, concise synthetic routes to several 3,6-anhydro sugar natural products are reported, including furanodictine A and sauropunols A-D.

Photoredox-Catalyzed Site-Selective α-C(sp3)?H Alkylation of Primary Amine Derivatives

The synthetic utility of tertiary amines to oxidatively generate α-amino radicals is well established, however, primary amines remain challenging because of competitive side reactions. This report describes the site-selective α-functionalization of primary amine derivatives through the generation of α-amino radical intermediates. Employing visible-light photoredox catalysis, primary sulfonamides are coupled with electron-deficient alkenes to efficiently and mildly construct C?C bonds. Interestingly, a divergence between intermolecular hydrogen-atom transfer (HAT) catalysis and intramolecular [1,5] HAT was observed through precise manipulation of the protecting group. This dichotomy was leveraged to achieve excellent α/δ site-selectivity.