159495-64-4

Usage

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

Upstream product

• 448217-88-7 Acetic acid (1R,2R,3R,4R,5R)-2-acetoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 
• 448217-84-3 Acetic acid (1R,2R,3R,5R)-4-oxo-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester 
• 19879-84-6 2,3,4,6-tetra-O-acetyl-1-thio-D-galactopyranose 
• 448217-86-5 Acetic acid (1R,2R,3R,4R,5R)-2-acetoxy-3-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester 
• 448217-82-1 Acetic acid (1R,2R,3R,5R)-4-oxo-3-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-6,8-dioxa-bicyclo[3.2.1]oct-2-yl ester 
• 19879-84-6 tetraacetyl thioglucose 
• 175652-49-0 ((2R,3R,4S,5R,6S)-2-[(acetyloxy)methyl]-6-{[(3aR,5R,6S,6aS)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-yl]sulfanyl}oxane-3,4,5-triyl triacetate) 
• 55951-90-1 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 
• 28251-80-1 3-S-acetyl-1,2:5,6-di-O-isopropylidene-3-deoxy-3-thio-α-D-glucofuranose 
• 175652-45-6 1,2,4,6-tetra-O-acetyl-3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thio-α-D-glucopyranose 
• 175652-46-7 1,2,4,6-tetra-O-acetyl-3-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thio-β-D-glucopyranose 
• 62860-10-0 2,3,4,6-tetra-O-acetyl-1-S-acetyl-1-thio-α-D-glucopyranoside 
• 63073-99-4 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol 

Relevant academic research and scientific papers

Thiosugars VI: A simple stereoselective approach to (1→3)-3-S-thiodisaccharides from levoglucosenone

A new stereoselective synthesis of (1→3)-3-S-thiodisaccharides is described. Levoglucosenone-derived chiral building blocks produced by the selenium-mediated iodination at C-3 afforded 3-iodoketones in moderate yield. Iodine displacement with sulfur nucleophiles (1-thiols) resulted in 3-thiodisaccharides. Following reduction of the C-2 keto function constituted a new two-step general approach to these biologically important thiosugars.

Synthesis of sulfur-linked analogues of nigerose, laminarabiose, laminaratriose, gentiobiose, gentiotriose, and laminaran trisaccharide Y

Sulfur-linked analogues of 3-O-α-D-glucopyranosyl-D-glucose (nigerose), 3-O-β-D-glucopyranosyl-D-glucose (laminarabiose), 6-O-β-D-glucopyranosyl-D-glucose (gentiobiose), O-β-D-glucopyranosyl-(1 → 3)-O-β-D-glucopyranosyl-(1 → 3)-D-glucose (laminaratriose), O-β-D-glucopyranosyl-(1 → 6)-O-β-D-glucopyranosyl-(1 → 6)-D-glucose (gentiotriose) and 3,6-di-O-β-D-glucopyranosyl-D-glucose (laminaran trisaccharide Y), namely, respectively, 3-thionigerose (6), 3-thiolaminarabiose (II), 6-thiogentiobiose (21), 3(I),3(II)-dithiolaminaratriose (16), 6(I),6(ii)-dithiogentiotriose (29) and 3(I),6(I)-dithiolaminaran trisaccharide Y (37) have been conveniently prepared by S(N)2 reactions of the corresponding anomer of D-glucopyranose 1-thiolate with suitably activated monosaccharide derivatives in N,N-dimethylformamide (for 6 and 21) or in tetrahydrofuran in the presence of a crown ether (for 11). A sequence involving the reaction of non-anomeric thiolates with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide was alternatively used for the preparation of 11 and 21 but proved less satisfactory. The preparation of thiotrisaccharides 16, 29, and 37 involved a mixed approach.

α-(1->2)-, α-(1->3)-, and α-(1->6)-Linked thioglycosidic disaccharides: syntheses and anti-HIV testing of thiokojibiose octaacetate, thionigerose, and thioisomaltose

The syntheses of several α-linked thioglycosidic disaccharides are described, including thiokojibiose octaacetate (1), thionigerose (2), and thioisomaltose (3).The title compounds were synthesized by coupling 2,3,4,6-tetra-O-acetyl-1-S-acetyl-1-thio-α-D-g