127243-54-3

Upstream product

• 139070-96-5 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(methylene)-α-D-xylo-hexopyranoside 
• 139070-99-8 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(formyl)-α-D-galactopyranoside 
• 127924-50-9 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-C-(hydroxymethyl)-α-D-galactopyranoside 
• 98807-61-5 1-O-methyl-2,3,6-tri-O-benzyl-4-keto-α-D-glucopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 127214-51-1 methyl 2,3,6-Tri-O-Benzyl-4-Deoxy-4-Formyl-α-D-Gluco-Pyranoside 
• 3396-99-4 methyl α-D-galactopyranoside 
• 127924-45-2 (2R,3S,4R,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-3-trimethylsilanylethynyl-tetrahydro-pyran-3-ol 
• 127924-41-8 (2R,4R,5R,6S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-methoxy-dihydro-pyran-3-one 
• 100-39-0 benzyl bromide 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 127214-51-1 (2S,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-carbaldehyde 
• 127924-51-0 (2S,3R,4S,5R,6S)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-(2,2-dibromo-vinyl)-2-methoxy-tetrahydro-pyran 
• 127924-52-1 (3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-ylethynyl)-tetrahydro-pyran-2-ol 
• 127924-53-2 C₆₄H₆₆O₁₀ 
• 138459-11-7 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(iodomethyl)-α-D-glucopyranoside 
• 138459-06-0 Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside 
• 138459-05-9 Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-6-O-(tert-butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside 
• 139071-07-1 Methyl 2',6-Anhydro-2,3-di-O-benzyl-4-deoxy-4-C-(3',4',5',7'-tetra-O-benzyl-1'-deoxy-α-D-gluco-2-heptulopyranos-1'-yl)-α-D-glucopyranoside 
• 139071-04-8 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-4-C-(3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-2-heptulopyranos-1-yl)-α-D-glucopyranoside 
• 138459-00-4 Methyl 4-deoxy-4-C-(triphenylmethylenephosphonium iodide)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 139071-05-9 Methyl 4-C-(6-O-Acetyl-3,4,5,7-tetra-O-benzyl-2-heptulo-D-glucos-1-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside 
• 138459-02-6 (Z)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose 
• 138459-02-6 (E)-6,5-Di-O-(tert-butyldimethylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose 
• 138459-04-8 (Z)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexopyranosid-4-yl)-D-gluco-hex-1-enose 

Relevant academic research and scientific papers

Preferred conformation of C-lactose at the free and peanut lectin bound states

A conformational analysis of methyl α-C-lactoside (5) is carried out (Table 1), which suggests the preferred solution conformation of 5 to be described as a mixture of conformers A (φ = 300°; ψ = 60°) and B (φ = 300°; ψ = 300°) to a first approximation. A

The UDP-Galp mutase catalyzed isomerization: Synthesis and evaluation of 1,4-anhydro-β-d-galactopyranose and its [2.2.2] methylene homologue

The synthesis of 1,4-anhydro-β-d-galactopyranose (1,5-anhydro-α- d-galactofuranose), a proposed intermediate in the ring contraction isomerisation catalyzed by UDP-galactopyranose mutase, together with its [2.2.2] bicyclic methylene homologue, synthesised as a possible competitive inhibitor or alternative substrate, are reported. Neither compound was found to be an inhibitor or substrate for UDP-galactopyranose mutase from Klebsiella pneumoniae.

A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers

A wide variety of tert-butyldimethylsilyl ethers 1 can be easily cleaved to the corresponding parent hydroxyl compound 2 in the presence of 5 mol % of acetonyltriphenylphosphonium bromide (ATPB) at room temperature. In addition, tert-butyldiphenylsilyl ethers can also be cleaved by using 20 mol % of the same catalyst. Alkyl tert-butyldimethylsilyl ethers can be deprotected to the hydroxyl compounds chemoselectively in the presence of aryl tert- butyldimethylsilyl ethers. Some of the major advantages are mild reaction conditions, no aqueous workup, high efficiency and chemoselectivity and compatibility with other protecting groups; no brominations occur in the aromatic ring under these experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

A catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol is a good combination for the cleavage of tetrahydropyranyl (THP) and tert-butyldimethylsilyl (TBS) ethers

Various THP and TBS ethers can be unmasked easily to the corresponding hydroxyl compounds in good yields by using a combination of a catalytic amount of nickel(II) chloride hexahydrate and 1,2-ethanedithiol at room temperature. In addition, alkyl TBS ethers can be hydrolyzed chemoselectively in the presence of aryl TBS ethers. Moreover, alkyl TBS ethers can be cleaved easily in the presence of alkyl or aryl THP ethers using the same conditions.

A Highly Efficient and Chemoselective Synthetic Protocol for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols

Various alcohols and phenols can be converted efficiently to the corresponding tetrahydropyranyl (THP) ethers in good yields using catalytic amounts of bromodimethylsulfonium bromide (0.005-0.02 equivalent) at room temperature. On the other hand, various THP ethers can also be deprotected to the parent alcoholic or phenolic compounds in CH2Cl2/ MeOH (5:2) by employing 0.05 equivalent of the same catalyst. Some of the major advantages of this procedure are its mild conditions, that it is highly selective and efficient, high yielding, and cost-effective, that it needs no solvent and is compatible with the presence of other protecting groups. Furthermore, no brominations occur at a double or triple bond, at an allylic position or even at an aromatic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

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.

Steric Effects Are Not the Cause of the Rate Difference in Hydrolysis of Stereoisomeric Glycosides

(Equation presented) A long-lived and plausible explanation as to why glycosides with axial substituents are more reactive than those with equatorial substituents was given in 1955 by Edward based on sterical hindrance being relieved in the transition state. Using model compounds 5, 6, 8, and 10, we here show conclusively that sterical hindrance not is the controlling factor in glycoside hydrolysis.

α-glucosidase inhibitors

This invention relates to novel polyglycosidyl derivatives of 1-deoxy-nojirimycin, to the processes for their preparation and to their end-use applications, particularly as to their use in the treatment of diabetes.

Spiroketal Synthesis. - A Case of Intramolecular Glycoside Bond Formation

From 4-O-unsubstituted glucose derivatives 1a, b the 4-hydroxymethyl-substituted glucose derivatives 9a, b were obtained via oxidation to the ketone, Wittig reaction with methylenetriphenylphosphorane, borane addition, and subsequent oxidation to yield th

α-glucosidase inhibitors

This invention relates to novel N-glycosyl derivatives of 1,4-dideoxy-1,4-imino-D-arabinitol, to the chemical processes for their preparation, to their α-glucosidase inhibiting properties, and to their end-use application in the treatment of diabetes, obe