39483-51-7

Basic information

• Product Name: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
• Synonyms: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside
• CAS NO: 39483-51-7
• Molecular Weight: 494.652
• Mol File: 39483-51-7.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside(39483-51-7)
• EPA Substance Registry System: ethyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside(39483-51-7)

Safety Data

• Hazardous Substances Data: 39483-51-7(Hazardous Substances Data)

Upstream product

• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 
• 157758-63-9 ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside 
• 32934-24-0 S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside 
• 1415590-58-7 ethyl 2,3,4-tri-O-benzyl-6-O-picolinyl-1-thio-β-D-glucopyranoside 
• 128643-87-8 ethyl 1-thio-6-O-(triphenylmethyl)-β-D-glucopyranoside 
• 7473-36-1 ethyl 1-thio-β-D-glucopyranoside 
• 197853-41-1 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 20701-61-5 ethyl 4,6-O-benzylidene-1-thio-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 144368-77-4 ethyl 2,3,4-tri-O-benzyl-1-thio-6-O-(triphenylmethyl)-β-D-glucopyranoside 
• 152964-70-0 ethyl 2,3-di-O-benzyl-1-thio-β-D-glucopyranoside 
• 316188-11-1 ethyl 6-O-[(tert-butyl)diphenylsilyl]-1-thio-α-D-mannopyranoside 
• 128850-48-6 ethyl 1-thio-6-O-triphenylmethyl-α-D-mannopyranoside 
• 218937-71-4 ethyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Downstream Products

• 83921-84-0 ethyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 39483-54-0 ethyl O-(2,3,4-tri-O-benzyl-6-O-p-nitrobenzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 85011-43-4 ethyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 85011-42-3 ethyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 150592-17-9 tert-Butyl-diphenyl-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silane 
• 241471-07-8 ethyl 2,3,4-tri-O-benzyl-6-O-(3-bromomethyl-4,6-diphenylbenzyl)-1-thio-β-D-glucopyranoside 
• 440644-86-0 (2S,4R)-4-((2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxycarbonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester 2-pentafluorophenyl ester 
• 39604-21-2 [(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-ethylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-yl]-methanol 
• 128850-51-1 ethyl 2,3,4-tri-O-benzyl-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside 
• 33639-75-7 2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranose 

Relevant articles and documents

A highly efficient and useful synthetic protocol for the cleavage of tert-butyldimethylsilyl (TBS) ethers using a catalytic amount of acetyl chloride in dry methanol

A wide variety of tert-butyldimethylsilyl (TBS) ethers as well as tert-butyldiphenylsilyl (TBDPS) ethers 1 can be easily deprotected to the corresponding parent hydroxyl compounds 2 by employing catalytic amounts of acetyl chloride in dry MeOH at 0°C to room temperature in good yields. Some of the major advantages are mild conditions, high efficiency, high selectivity, high yields, easy operation, and also compatibility with other protecting groups. Furthermore, no acetylation nor chlorination takes place under the experimental conditions.

Picoloyl protecting group in synthesis: Focus on a highly chemoselective catalytic removal

The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts. This journal is

Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides

A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.