32934-24-0

Basic information

• Product Name: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside
• Synonyms: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside
• CAS NO: 32934-24-0
• Molecular Weight: 392.427
• Mol File: 32934-24-0.mol
• Article Data: 62

Chemical Properties

• CAS DataBase Reference: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside(32934-24-0)
• EPA Substance Registry System: ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α,β-D-glucopyranoside(32934-24-0)

Safety Data

• Hazardous Substances Data: 32934-24-0(Hazardous Substances Data)

Upstream product

• 75-08-1 ethanethiol 
• 83-87-4 β-D-mannopyranose pentaacetate 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 83-87-4 D-Mannose pentaacetate 
• 7647-01-0 hydrogenchloride 
• 3458-28-4 D-Mannose 
• 530-26-7 D-Mannose 
• 108-24-7 acetic anhydride 
• 75-03-6 ethyl iodide 
• 4490-94-2 3,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(ethoxycarbothioyl)sulfanyl] tetrahydro-2H-pyran-4-yl-acetate 
• 128962-63-0 ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 136758-06-0 ethyl 2,3,4-tri-O-benzyl-1-thio-β-L-rhamnopyranoside 
• 127753-95-1 ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 

Downstream Products

• 7473-36-1 ethyl 1-thio-α-D-mannopyranoside 
• 118627-56-8 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 139921-55-4 Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 139921-54-3 Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside 
• 137438-91-6 C₅₀H₄₆O₁₆ 
• 32934-24-0 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glycopyranoside 
• 155814-72-5 (2R,3S,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 406946-95-0 ethyl 2,3,4,6-tetra-O-acetyl-S-(N-tosylimino)-1-thio-α-D-mannopyranoside 
• 216859-54-0 ethyl 2,3,4,6-tetra-O-acetyl-S-(N-tosylimino)-1-thio-β-D-glucopyranoside 
• 4692-12-0 1,3,4,6-tetra-O-acetyl glucopyranose 
• 38992-99-3 methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranoside 

Relevant articles and documents

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

A versatile approach to the synthesis of glycans containing mannuronic acid residues

Reported herein is a new method for a highly effective synthesis of β-glycosides from mannuronic acid donors equipped with the 3-O-picoloyl group. The stereocontrol of glycosylations was achieved by means of the H-bond-mediated aglycone delivery (HAD). The method was utilized for the synthesis of a tetrasaccharide linkedviaβ-(1 → 3)-mannuronic linkages. We have also investigated 3,6-lactonized glycosyl donors that provided moderate to high β-manno stereoselectivity in glycosylations. A method to achieve complete α-manno stereoselectivity with mannuronic acid donors equipped with 3-O-benzoyl group is also reported.

Developing a library of mannose-based mono-and disaccharides: A general chemoenzymatic approach to monohydroxylated building blocks

Regioselective deprotection of acetylated mannose-based mono-and disaccharides differently functionalized in anomeric position was achieved by enzymatic hydrolysis. Candida rugosa lipase (CRL) and Bacillus pumilus acetyl xylan esterase (AXE) were immobilized on octyl-Sepharose and glyoxyl-agarose, respectively. The regioselectivity of the biocatalysts was affected by the sugar structure and functionalization in anomeric position. Generally, CRL was able to catalyze regioselective deprotection of acetylated monosaccharides in C6 position. When acetylated disaccharides were used as substrates, AXE exhibited a marked preference for the C2, or C6 position when C2 was involved in the glycosidic bond. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monohydroxylated building blocks that could be used as intermediates for the synthesis of mannosylated glycoconjugate vaccines targeting mannose receptors of antigen presenting cells.