20688-90-8

Basic information

• Product Name: METHYL-4,6-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE
• Synonyms: METHYL-4,6-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE;METHYL-4,6-O-ISOPROPYLIDENE-SS-D-GALACTOPYRANOSIDE
• CAS NO: 20688-90-8
• Molecular Formula: C₁₀H₁₈O₆
• Molecular Weight: 234.24632
• Mol File: 20688-90-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL-4,6-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL-4,6-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE(20688-90-8)
• EPA Substance Registry System: METHYL-4,6-O-ISOPROPYLIDENE-BETA-D-GALACTOPYRANOSIDE(20688-90-8)

Safety Data

• Hazardous Substances Data: 20688-90-8(Hazardous Substances Data)

Upstream product

• 67-64-1 acetone 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 72813-11-7 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranoside 
• 116-11-0 2-Methoxypropene 
• 77-76-9 2,2-dimethoxy-propane 
• 97-30-3 methyl D-glucopyranoside 

Downstream Products

• 81348-23-4 Acetic acid (2R,3S,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-methoxy-tetrahydro-pyran-4-yl ester 
• 81348-24-5 methyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranoside 
• 6988-40-5 methyl 2,3-di-O-benzyl-β-D-galactopyranoside 
• 122079-62-3 methyl 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-β-D-glucopyranoside 
• 122079-83-8 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-6-O-propionyl-α-D-glucopyranosyl)-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol 
• 122079-84-9 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-α-D-glucopyranosyl)-2,5-dideoxy-L-iditol 
• 122079-61-2 methyl 2,3-di-O-benzyl-4-O-methanesulfonyl-6-O-propionyl-β-D-galactopyranoside 
• 122079-60-1 methyl 2,3-di-O-benzyl-6-O-propionyl-β-D-galactopyranoside 
• 122079-59-8 methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-β-D-galactopyranoside 

Relevant articles and documents

Oenothein B, dimeric hydrolysable tannin inhibiting HCV invasion from Oenothera erythrosepala

The envelope proteins of the hepatitis C virus (HCV), E1 and E2, have been revealed to be essential for invasion of HCV. Thus, we were engaged in the search for the inhibitors against HCV invasion through the assay system using the model virus expressing recombinant HCV envelopes, E1 and E2. Now, we disclosed dimeric hydrolysable tannin oenothein B (1) from MeOH extract of Oenothera erythrosepala as an active principle for inhibition of HCV invasion and its potency was almost the same as that of monomeric hydrolysable tannin, tellimagrandin I (2). Furthermore, by use of stereoselectively prepared 1-β- and 1-α-O-methyl tellimagrandin Is (4 and 5), the introduction of methyl moiety into 1-hydroxy group of 2 was clarified to result in slightly reduction of activity and β-isomer was revealed to exhibit a little stronger activity than α-one.

Synthesis of sorbistin analogues.

D-Galactose was converted into the glycosylating agents 4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-alpha-D-glucopyranosyl chloride (11) and the methyl beta-D-thiopyranoside 19. Condensation of 11 with 2,5-diazido-1,6-di-O-benzoyl-2,5-di-deoxy-L-iditol in the presence of mercury salts gave 24% of 2,5-diazido-3-O-(4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-alp ha-D- glucopyranosyl)-1,6-di-O-benzoyl-2,5-dideoxy-L-iditol. Methyl trifluoromethanesulfonate-promoted glycosylation of 1,3-diazido-2-O-benzyl-1,3-dideoxy-5,6-O-isopropylidene-D-gulit ol with 19 in the presence of 2,6-di-tert-butyl-4-methylpyridine gave 1,3-diazido-4-O-(4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-alp ha-D- glucopyranosyl)-2-O-benzyl-1,3-dideoxy-5,6-O-isopropylidene-D-gulitol (42), whereas, in the absence of base, migration of the O-isopropylidene group occurred, affording 1,3-diazido-6-O-(4-azido-2,3-di-O-benzyl-4-deoxy-6-O-propionyl-alp ha-D- glucopyranosyl)-2-O-benzyl-1,3-dideoxy-4,5-O-isopropylidene-D-gulitol in addition to 42.

The Deoxygenation of Some Carbohydrate Diols via Derived Cyclic Thiocarbonate

The treatment of methyl 2,6-di-O-methyl-3,4-O-thiocarbonyl-β-D-galactoside with methyl iodide gives mainly the 3-deoxy-3-iodo-D-guloside, whereas the α-anomer of the above and methyl 2-O-methyl-3,4-O-thiocarbonyl-β-L-arabinoside give mainly the 4-deoxy-4-

NEW RESULTS IN THE ISOPROPYLIDENATION OF GALACTOPYRANOSIDES. USEFUL INTERMEDIATES FOR THE SYNTHESIS OF GALACTOSE DERIVATIVES.

Reaction of several α- and β-galactopyranosides with 2,2-dimethoxypropane produced up to five types of mono-, bis-, and tris(isopropylidene)acetals, among which the 3,4-O-isopropylidene-6-O-(2-methoxyisopropyl) derivatives can be obtained in high yield an

PROPERTIES OF (13)C-N.M.R. SPECTRA OF O-(1-CARBOXYETHYLIDENE) DERIVATIVES OF METHYL β-D-GALACTOPYRANOSIDE: MODELS FOR DETERMINATION OF PYRUVIC ACID ACETAL STRUCTURES IN POLYSACCHARIDES

(13)C-N.m.r. spectra were recorded of compounds containing O-(1-carboxyethylidene) groups linked to galactopyranose and fucopyranose derivatives.These compounds are useful as aids in determination of the positions and configurations of pyruvic acid acetal substituents in polysaccharides.Chemical shifts of non-protonated acetal carbons depend on whether the acetal ring is 5-membered (δc 107-109.5) or 6-membered (δc 100.5-102.4).The C-3 signals of 3,4-(1-carboxyethylidene) acetals are typical, being at ca. δc 81 and in the case of the barium salt of the methyl β-D-galactopyranoside derivative.The exact value depends on the configuration, whether it is an in 6 (δc 81.1) or 5 (δc 80.4).The CH3 signals of proton-n.m.r. spectra are also diagnostically useful, falling at δ 1.97 and 2.07 respectively. (The foregoing shift-values are pH dependent).The pyruvylated galactan from the snail, Pomacea lineata, was shown to contain some residues that could be assigned a structure corresponding, in the position of acetal substitution and acetal configuration, to structure 6.Compound 6 (barium salt) is of interest as its (13)C-n.m.r. spectrum lacks non-protonated carbonyl and acetal carbon resonances, when obtained by the usual procedures.While this is principally because of long T1 values, the non-protonated acetal carbon signals are comparatively broad, possibly through slow conformational interchange.In the case of the carbonyl resonance, the lack of sensitivity is because of a low n.O.e. value of 1.4, approximately one half that of other carbon atoms in the molecule.