142048-02-0

Basic information

• Product Name: benzyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1-4)-β-D-xylopyranoside
• CAS NO: 142048-02-0
• Molecular Weight: 818.831
• Mol File: 142048-02-0.mol

Chemical Properties

• CAS DataBase Reference: benzyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1-4)-β-D-xylopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1-4)-β-D-xylopyranoside(142048-02-0)
• EPA Substance Registry System: benzyl O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1-4)-β-D-xylopyranoside(142048-02-0)

Safety Data

• Hazardous Substances Data: 142048-02-0(Hazardous Substances Data)

Upstream product

• 627466-84-6 2,3,4,6-tetra-O-benzoyl-D-galactose 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 100-51-6 benzyl alcohol 
• 10548-61-5 benzyl-β-D-xylopyranoside 
• 138479-80-8 Benzyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-xylopyranoside 
• 61198-88-7 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 
• 138515-35-2 Benzyl 2,3-O-isopropylidene-β-D-xylopyranoside 
• 10548-53-5 benzyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 
• 149707-75-5 2,3,4,6-tetra-O-benzoyl-1-O-trichloroacetimidoyl-α-D-galactopyranose 

Downstream Products

• 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 
• 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 
• 138479-92-2 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 

Relevant articles and documents

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.