31899-66-8

Usage

InChI:InChI=1/C7H14O4/c1-4-5(8)3-6(9)7(10-2)11-4/h4-9H,3H2,1-2H3/t4-,5+,6-,7+/m1/s1

Upstream product

• 77770-59-3 methyl 3,6-dibromo-3,6-dideoxy-α-D-allo-hexopyranoside 
• 49617-11-0 methyl-[tetrakis-O-(toluene-4-sulfonyl)-α-D-glucopyranoside] 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 1128-40-1 methyl α-D-fucopyranoside 
• 99310-37-9 methyl 3,6-dideoxy-2-O-p-tolylsulfonyl-α-D-xylo-hexopyranoside 
• 99310-36-8 methyl 6-deoxy-2,3-di-O-p-tolylsulfonyl-α-D-galactopyranoside 
• 99310-39-1 methyl 3,6-dideoxy-2-O-p-tolylsulfonyl-α-D-erythro-hexopyranosid-4-ulose 
• 74052-05-4 methyl 2,3,6-tri-O-p-tolylsulfonyl-α-D-galactopyranoside 
• 169218-38-6 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-methanesulfonyl-α-D-glucopyranoside 
• 28642-64-0 methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside 
• 169048-75-3 methyl 6-S-acetyl-2,4-di-O-benzoyl-6-deoxy-3-O-methanesulfonyl-6-thio-α-D-glucopyranoside 
• 169048-74-2 methyl 2,4-di-O-benzoyl-6-bromo-6-deoxy-3-O-methanesulfonyl-α-D-glucopyranoside 
• 169048-76-4 methyl 3,6-anhydro-3-thio-α-D-glucopyranoside 

Downstream Products

• 496-79-7 (6-deoxy-3-O-methyl)-D-allose 
• 1417721-80-2 C₂₅H₃₂O₆ 
• 1417721-81-3 (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran α-anomer 
• 1417721-82-4 (3R,5S,6R)-3,5-bis(benzyloxy)-2-((R)-hex-5-en-2-yloxy)-6-methyltetrahydro-2H-pyran β-anomer 
• 1417721-64-2 C₂₂H₂₄Cl₃NO₄ 
• 188254-16-2 (2R,3R,5R,6S)-6-Methoxy-2-methyl-3-((1R,3S,4R,5S,6R)-4,5,6,7-tetrakis-benzyloxy-1,3-dimethoxy-heptyl)-tetrahydro-pyran-3,5-diol 
• 188254-20-8 (3R,4S,5R,6S)-4,5,6,7-Tetrakis-benzyloxy-1-[(2R,3R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl]-3-methoxy-heptan-1-one 
• 188254-10-6 (3S,4R,5S,6R)-4,5,6,7-Tetrakis-benzyloxy-1-[(2R,3R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl]-3-methoxy-heptan-1-one 
• 188254-15-1 (2R,3R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((1R,3S,4R,5S,6R)-4,5,6,7-tetrakis-benzyloxy-1,3-dimethoxy-heptyl)-tetrahydro-pyran-3-ol 
• 188254-21-9 (2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((1S,3R,4S,5R,6S)-4,5,6,7-tetrakis-benzyloxy-1-hydroxy-3-methoxy-heptyl)-tetrahydro-pyran-3-ol 
• 188254-11-7 (2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((1S,3S,4R,5S,6R)-4,5,6,7-tetrakis-benzyloxy-1-hydroxy-3-methoxy-heptyl)-tetrahydro-pyran-3-ol 
• 188254-22-0 (2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((1R,3R,4S,5R,6S)-4,5,6,7-tetrakis-benzyloxy-1-hydroxy-3-methoxy-heptyl)-tetrahydro-pyran-3-ol 
• 188254-12-8 (2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-2-methyl-3-((1R,3S,4R,5S,6R)-4,5,6,7-tetrakis-benzyloxy-1-hydroxy-3-methoxy-heptyl)-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Reactivity–Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides

The assembly of complex bacterial glycans presenting rare structural motifs and cis-glycosidic linkages is significantly obstructed by the lack of knowledge of the reactivity of the constituting building blocks and the stereoselectivity of the reactions i

Structural reassignment, absolute configuration, and conformation of hypurticin, a highly flexible polyacyloxy-6-heptenyl-5,6-dihydro-2H-pyran-2-one

The structural reassignment, absolute configuration, and conformational behavior of the highly flexible natural product hypurticin (pectinolide E), 6S-[3′S,5′R,6′S-triacetoxy-1Z-heptenyl]-5S-acetoxy-5, 6-dihydro-2H-pyran-2-one (1), were ascertained by a m

Synthesis of three Salmonella epitopes for biosensor studies of carbohydrate-antibody interactions

Disaccharides 1-3 corresponding to the antigenic determinants of Salmonella serotypes A, B, and D1 were synthesized in a form suited for use in biosensors. The disaccharide determinants each contain a unique 3,6-dideoxyhexose, namely abequose (

3,6-Thioanhydro sugars as important key intermediates in the enantiospecific synthesis of chiral polyhydroxythiolanes

Methyl 3,6-thioanhydro-α-D-glucopyranoside (5) was obtained in seven steps from the commercially available methyl α-D-glucopyranoside. Transformation of 5 into (2R,3R,4S)-3,4-dihydroxy-2-[(S)-1,2-dihydroxyethyl]thiolane (9) was achieved by acid hydrolysis

Reactions of p-Toluenesulfonates with Lithium Triethylborohydride. Visible and Hidden Rearrangements

The reaction of methyl 6-deoxy-2,3-di-O-p-tolylsulfonyl-α-D-galactopyranoside (4) with lithium triethylborohydride (LTBH) gives three primary products, all of which result from rearrangement.One of these, methyl 5-deoxy-3-C-(hydroxymethyl)-2-O-p-tolylsulfonyl-α-D-xylofuranoside (7), arises from ring contraction while the other two, methyl 3,6-dideoxy-2-O-p-tolylsulfonyl-α-D-xylo- (5) and -ribo-hexopyranosides (9), result from hydride migration and reduction of the resulting ketone, methyl 3,6-dideoxy-2-O-p-tolylsulfonyl-α-D-erythro-hexopyranosid-4-ulose (8).Photolysis of compounds 4, 5, and 9 removes the tosyl groups.

Reactions of Partially Acylated Aldohexopyranosides, II. - Regioselective Oxidation of Partially Acylated Aldohexopyranosides with Pyridinium Chlorochromate and a New Photochemical Method for the Preparation of Methyl 3,6-Dideoxy-α-D-ribo-hexopyranoside

Regioselective oxidation of methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside (1) with pyridinium chlorochromate yields methyl 2,6-di-O-pivaloyl-α-D-ribo-hexopyranosid-3-ulose (2) as well as a ten-membered cyclic diester.If methyl 3,6-di-O-benzoyl- (7) and met

Conversion of hydroxyl groups into bromo groups in carbohydrates with inversion of configuration

A novel reagent system is described for the efficient, one-step transformation of hydroxyl groups in carbohydrates to bromodeoxy groups.The reaction proceeds with inversion of configuration.The reagent system consists of triphenylphosphine, tribromoimidazole, and imidazole in toluene at elevated temperature.The carbohydrate need not be soluble in toluene.The examples given include substitution of isolated primary and secondary hydroxyl groups in otherwise protected carbohydrates as well as disubstitution involving one primary and one secondary position in hexopyranosides.High yields are obtained in the replacement of hydroxyl by brommine in the 2-position of 3,4,6-protected methyl α-D-gluco- and -mannopyranosides.