6087-40-7

Basic information

• Product Name: (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran
• Synonyms: (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran
• CAS NO: 6087-40-7
• Molecular Weight: 304.297
• Mol File: 6087-40-7.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran(6087-40-7)
• EPA Substance Registry System: (2R,3S,4R,6S)-3,4-diacetoxy-2-(acetoxymethyl)-6-methoxytetrahydro-2H-pyran(6087-40-7)

Safety Data

• Hazardous Substances Data: 6087-40-7(Hazardous Substances Data)

Upstream product

• 126873-07-2 methyl 3,4,6-tri-O-acetyl-2-deoxy-α/β-D-glucopyranoside 
• 67-56-1 methanol 
• 2873-29-2 D-glucal triacetate 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 925683-96-1 (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran-3-ol 
• 925683-97-2 (2R,3S,4R,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxy-3-{[(methylsulfanyl)carbothioyl]oxy}tetrahydro-2H-pyran 
• 925683-99-4 (2S,4S,6S)-4-(benzyloxy)-2-methoxy-6-(tosyloxymethyl)tetrahydro-2H-pyran 
• 925684-01-1 (2S,4S,6R)-4-(benzyloxy)-2-methoxy-6-undecyltetrahydro-2H-pyran 
• 925684-02-2 (2S,4S,6R)-4-(benzyloxy)-6-undecyltetrahydro-2H-pyran-2-ol 
• 925684-04-4 (4S,6R)-4-(benzyloxy)-6-undecyltetrahydro-2H-pyran-2-one 
• 925684-05-5 methyl (3S,5R)-3-(benzyloxy)-5-(methoxymethoxy)hexadecanoate 
• 6752-48-3 (4aR,6S,8R,8aS)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol 
• 104872-04-0 Orlistat 
• 68711-40-0 (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone 
• 87391-88-6 [(2S,4S,6S)-4-(benzyloxy)-6-methoxytetrahydro-pyran-2-yl]-methanol 
• 80667-89-6 (4aR,6S,8R,8aS)-8-(benzyloxy)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine 
• 119874-56-5 (2R,3S,4R,6S)-4-(benzyloxy)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3-ol 
• 614752-28-2 (2S,4S,6S)-4-(benzyloxy)-2-[(tert-butyldimethylsiloxy)methyl]-6-methoxytetrahydro-2H-pyran 

Relevant articles and documents

Ferric chloride, an anomerization catalyst for the preparation of alkyl α-glycopyranosides

Anhydrous FeCl3 in CH2Cl2 has been found to readily anomerize β-glycopyranosides to their corresponding α-anomers in good yields and selectivities at room temperatures. Acetyl- and benzoyl-protected oxygen sugars yielded the best results.

STRAIGHTFORWARD HOMOCHIRAL SYNTHESIS OF THE LACTONE MOIETY OF MEVINIC ACIDS

A new straightforward synthesis of the common lactone moiety of mevinic acids is described starting form tri-O-acetyl-D-glucal 2.The key diastereoselective O-glycosidation of 2 with methanol and subsequent methanolysis and tritylation are incorporated in

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

Ferrier rearrangement and 2-deoxy sugar synthesis from d-glycals mediated by layered α-zirconium sulfophenylphosphonate-methanphosphonate as heterogeneous catalyst

Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate- methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields. Graphical Abstract: [Figure not available: see fulltext.]

A chiron approach to (-)-tetrahydrolipstatin

An efficient chiron approach to the total synthesis of (-)- tetrahydrolipstatin is described. The main features of the synthetic strategy, which starts from tri-O-acetyl-D-glucal, are copper-mediated C-C bond formation, Frater alkylation, and Barton-McCombie deoxygenation. Georg Thieme Verlag Stuttgart.

Synthetic studies on antascomicin A: Construction of the C18-C34 fragment

Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of

Synthesis of a-ring synthon of 19-nor-1alpha,25-dihydroxyvitamin D3 from (D)-glucose

The present invention provides a method for the synthesis of an A-ring synthon phosphine oxide used in the preparation of 19-nor vitamin D compounds, and to novel synthetic intermediates formed during the synthesis. The new method prepares the phosphine oxide from (D)-glucose.

Novel synthesis of 2-substituted 19-norvitamin D A-ring phosphine oxide from D-glucose as a building block

19-Norvitamin D A-ring phosphine oxide 5 was synthesized by a new sequence mode starting from D-glucose as a chiral template. Transformation of the pyranoside ring into the A-ring carbocycle was achieved by the Pd-catalyzed Ferrier rearrangement. The phosphine oxide 5 was obtained in an 18% overall yield by this novel cost-effective method.