138515-35-2

Basic information

• Product Name: Benzyl 2,3-O-isopropylidene-β-D-xylopyranoside
• Synonyms: Benzyl 2,3-O-isopropylidene-β-D-xylopyranoside
• CAS NO: 138515-35-2
• Molecular Weight: 280.321
• Mol File: 138515-35-2.mol

Chemical Properties

• CAS DataBase Reference: Benzyl 2,3-O-isopropylidene-β-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 2,3-O-isopropylidene-β-D-xylopyranoside(138515-35-2)
• EPA Substance Registry System: Benzyl 2,3-O-isopropylidene-β-D-xylopyranoside(138515-35-2)

Safety Data

• Hazardous Substances Data: 138515-35-2(Hazardous Substances Data)

Upstream product

• 10548-53-5 benzyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 100-51-6 benzyl alcohol 
• 116-11-0 2-Methoxypropene 
• 10548-61-5 benzyl-β-D-xylopyranoside 

Downstream Products

• 478175-96-1 benzyl 2,3-O-isopropylidene-4-O-(N-phthalimido)-α-L-arabinoside 
• 138479-91-1 N-(Benzyloxycarbonyl)-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranosyl>-L-seryl-glycine allyl ester 
• 138479-94-4 N-(Benzyloxycarbonyl)-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranosyl>-L-seryl-glycine 
• 138479-93-3 C₆₁H₅₆N₂O₁₉ 
• 138479-82-0 2,3-Di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-xylopyranosyl trichloroacetimidate 
• 138479-81-9 Benzyl 2,3-O-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside 
• 142048-02-0 benzyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1-4)-β-D-xylopyranoside 
• 138479-92-2 O-<2,3-Di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranosyl>-N-(9-fluorenylmethoxycarbonyl)-L-seryl-glycine allyl ester 
• 138479-90-0 N-(Benzyloxycarbonyl)-O-<2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranosyl>-L-seryl-glycine benzyl ester 
• 159420-99-2 benzyl O-(benzyl 2,3,4-tri-O-benzyl-α-D-glucopyranosyluronate)-(1->4)-2,3-di-O-benzyl-β-D-xylopyranoside 
• 136136-35-1 benzyl 4-O-allyl-2,3-di-O-benzyl-β-D-xylopyranoside 
• 72185-76-3 benzyl 4-O-allyl-β-D-xylopyranoside 
• 136233-08-4 benzyl 2,3-di-O-benzyl-β-D-xylopyranoside 
• 478175-97-2 benzyl 4-O-(N-phthalimido)-α-L-arabinoside 

Relevant articles and documents

Rules for priming and inhibition of glycosaminoglycan biosynthesis; Probing the β4GalT7 active site

β-1,4-Galactosyltransferase 7 (β4GalT7) is an essential enzyme in the biosynthesis of glycosaminoglycan (GAG) chains of proteoglycans (PGs). Mammalian cells produce PGs, which are involved in biological processes such as cell growth and differentiation. T

The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine

The treatment of benzyl 2,3-O-isopropylidene-β-L-xylopyranoside with N-hydroxyphthalimide under Mitsunobu conditions, followed by protecting-group interchange, gave benzyl 4-O-[(tert-butoxycarbonyl)amino]-2,3-O-isopropylidene-α-D-arabinoside. Mild acid hydrolysis and catalytic hydrogenolysis afforded 4-O-[(tert-butoxycarbonyl)amino]-D-arabinose that, upon heating in water, gave the dihydrooxazine [(4R,5S,6R)-5,6-dihydro-4,5-dihydroxy-6-hydroxymethyl-4H-1,2-oxazine] as a crystalline solid. A single-crystal structure determination of this solid showed it to exist in the 5H6 conformation. Reduction of the dihydrooxazine gave the tetrahydrooxazine [(4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-2H-1,2-oxazine]. The dihydrooxazine was an effective inhibitor of two β-glucosidases (Ki = 27 and 35 μM). Benzyl 2,3-O-isopropylidene-β-L-xylopyranoside, via the derived imidazylate, was converted into a nitrile that, upon reduction and protecting-group manipulations, gave benzyl 4-C-aminomethyl-4-deoxy-α-D-arabinoside. Treatment of this amine with hydrogen and palladium-on-carbon gave isofagomine.

4-O-β-D-Galactopyranosyl-D-xylose: A new synthesis and application to the evaluation of intestinal lactase

4-O-β-D-Galactopyranosyl-D-xylose (2) was prepared from benzyl 2,3-O-isopropylidene-β-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the V(max) was 25% of that with lactose and the K(m) was 370 mM (cf. 27 mM for lactose). Oral administration of 2 to suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically. 4-O-β-D-Galactopyranosyl-D-xylose (2) was prepared from benzyl 2,3-O-isopropylidene-β-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the Vmax was 25% of that with lactose and the Ktu was 370mM (cf. 27mM for lactose). Oral administration of 2 to suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically.

Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans

2,3,4,6-Tetra-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate was condensed with benzyl 2,3-O-isopropylidene-β-D-xylopyranoside to give the corresponding β-(1->4)-linked disaccharide derivative, which was transformed into 2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-xylopyranosyl trichloroacetimidate.This glycosyl donor was condensed with a set of selectively C,N-protected L-seryl-glycine dipeptide units.Selective deblocking at the C- or N-termini of the glycosylated or non-glycosylated dipeptide segments, and coupling using the mixed-anhydride procedure allowed the construction in high yield of partially or fully glycosylated oligopeptides from the carbohydrate-protein linkage region of proteoglycans.