80441-61-8

Basic information

• Product Name: thiodigalactoside
• CAS NO: 80441-61-8
• Molecular Formula: C12H22O10S
• Molecular Weight: 358.3621
• Mol File: 80441-61-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 712.6°Cat760mmHg
• Flash Point: 384.7°C
• Appearance: /
• Density: 1.77g/cm³
• Vapor Pressure: 1.85E-23mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: thiodigalactoside(CAS DataBase Reference)
• NIST Chemistry Reference: thiodigalactoside(80441-61-8)
• EPA Substance Registry System: thiodigalactoside(80441-61-8)

Safety Data

• Hazardous Substances Data: 80441-61-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H22O10S/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5+,6+,7+,8+,9-,10-,11+,12+/m1/s1

Upstream product

• 5505-45-3 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 62778-20-5 sodium salt of 1-thio-α-D-glucopyranose 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 18968-44-0 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 5505-45-3 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 1393083-67-4 6-O-acetyl-2,3,4,2′,3′,4′,6′-hepta-O-benzyl-1-thio-α,α-D-trehalose 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 

Downstream Products

• 5505-45-3 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 

Relevant articles and documents

Synthesis of Symmetrical Dodeco-6,7-diuloses

Dodeco-6,7-diuloses represent a rare class of sugars and can be considered as anomerically linked di-hexoses with two hemiacetal functions in the middle. Herein, the synthesis of three symmetrical dodeco-6,7-diuloses (gluco-gluco, galacto-galacto, manno-manno) is described. For their preparation four synthetic strategies were pursued, whose mutual key step, the connection of the anomeric centers, is particularly emphasized. Specifically, C–C bond forming methods are employed, such as a Grubbs metathesis, a stannyl glycal homocoupling reaction, a coupling of a sulfinyl glycal with a sugar lactone and a Ramberg–B?cklund rearrangement. Since the ring closure via hemiacetal formation of the target compounds cannot be predicted, intensive NMR spectroscopic structure elucidation of the diuloses was performed.

An Expeditious Synthesis of 1-Thiotrehalose

A two-step synthesis of 1-thiotrehalose is reported. In the key TMSOTf-mediated double thioglycosylation step, the tri- O -benzyl 1,6-anhydro-D-glucose reactant behaves both as a glycosyl donor and a glycosyl acceptor precursor. In this highly convergent process, two carbon-sulfur bonds are created at the anomeric positions with a high level of stereocontrol.

A facile and highly stereoselective synthesis of 1-thiotrehalose

A facile and highly stereoselective synthesis of 1-thiotrehalose, that is, α,α-S-linked trehalose, is described. Glycosylation of configurationally pure α-glucosyl thiol 5 with glucosyl trichloroacetimidate 6 or glucosyl thioimidate 9 followed by deprotection afforded 1-thiotrehalose in excellent α-stereoselectivity and high yield. A different synthetic route to the key building block, α-glucosyl thiol 5, was also investigated in this report.