4613-78-9

Basic information

• Product Name: BETA-GENTIOBIOSE OCTAACETATE
• Synonyms: BETA-D-GENTIOBIOSE OCTAACETATE;BETA-GENTIOBIOSE OCTAACETATE;B-GENTIOBIOSE OCTAACETATE;GENTIOBIOSE OCTAACETATE, B;6-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL)-1,2,3,4-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE;6-O-BETA-D-GLUCOPYRANOSYL-D-GLUCOSE OCTAACETATE;6-O-(2,3,4,6-Tetra-O-acetyl-?D-glucopyranosyl)-1,2,3,4-tetra-O-acetyl-?D-glucopyranose;.beta.-D-Glucopyranose, 6-O-(2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl)-, tetraacetate
• CAS NO: 4613-78-9
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.59
• Mol File: 4613-78-9.mol
• Article Data: 17

Chemical Properties

• Melting Point: 191-195°C
• Boiling Point: 661.384 °C at 760 mmHg
• Flash Point: 272.155 °C
• Appearance: /
• Density: 1.37 g/cm³
• CAS DataBase Reference: BETA-GENTIOBIOSE OCTAACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: BETA-GENTIOBIOSE OCTAACETATE(4613-78-9)
• EPA Substance Registry System: BETA-GENTIOBIOSE OCTAACETATE(4613-78-9)

Safety Data

• Hazardous Substances Data: 4613-78-9(Hazardous Substances Data)

Usage

Uses

β-D-Gentiobiose octaacetate (CAS# 4613-78-9) is a useful disaccharide building block used in the synthetic preparation of leptosin, and used in the glycosylation of alcohols.

Upstream product

• 37074-90-1 1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 7792-95-2 O⁶-β-D-glucopyranosyl-α-D-glucopyranosyl fluoride 
• 7732-18-5 water 
• 127-09-3 sodium acetate 
• 108-24-7 acetic anhydride 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 
• 54325-28-9 6-O-trityl-D-glucopyranose 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 65620-65-7 1,2,3,4-tetra-O-acetyl-D-glucopyranose 
• 74808-10-9 2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate 
• 536-11-8 gentibiose 
• 13100-46-4 1,2,3,4-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 220041-69-0 phenyl-[O²,O³,O⁴-triacetyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside] 
• 1470074-07-7 C₃₄H₄₀F₃NO₁₈ 
• 1470074-08-8 C₃₆H₄₆O₂₁ 
• 1470074-09-9 C₂₂H₃₂O₁₄ 
• 1552275-50-9 C₃₇H₅₄O₁₃Si 
• 1448810-97-6 m-formyl-p-hydroxy-benzyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside 
• 1448810-91-0 m-formyl-p-hydroxy-benzyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→6)-2,3,4-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 1436870-80-2 cyclohexyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 1379664-83-1 (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1379664-82-0 (+)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3-di-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 
• 1022927-33-8 (+)-menthyl 2,3,4-tri-O-acetyl-6-O-[2,3-di-O-acetyl-4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 
• 1022927-17-8 tert-butyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 
• 1022927-05-4 (-)-menthyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 
• 1022927-00-9 (+)-menthyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside 

Relevant articles and documents

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Deuterium labelling to extract local stereochemical information by VCD spectroscopy in the C-D stretching region: A case study of sugars

Stereochemical elucidation of molecules with multiple chiral centers is difficult. Even with VCD spectroscopy, excluding all but one diastereomeric structural candidate is challenging because the stereochemical inversion of one chiral center among many centers does not always result in noticeable differences in their VCD spectra. This work demonstrates that the introduction of a suitable VCD chromophore with absorption in the 2300-1900 cm-1 region can be used for extracting local stereochemical information and for the stereochemical assignment of the C-1 position of various sugars as a case study. Through studies on a series of epimeric pairs of monosaccharides and their derivatives, we found that the introduction of one -OCD3 group to each C-1 position produced almost mirror-image VCD patterns in the 2300-1900 cm-1 region depending on the C-1 stereochemistry irrespective of the other molecular moieties. This work also shows that comparison of the observed VCD signals and the calculated ones enables the stereochemical assignment of a chiral center in the vicinity of the chromophore. This study provides a proof of concept that the use of a VCD chromophore in the 2300-1900 cm-1 region enables the analysis of selected stereochemistry of suitable molecular systems. Further studies on this concept should lead to the development of a method useful for the structural elucidation of other types of complex molecules.

Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A: Via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors

A convergent synthesis of the complex, doubly-branched pentasaccharide domain of the natural-product immunoadjuvant jujuboside A is described. The key step is a sterically-hindered glycosylation reaction between a branched trisaccharide trichloroacetimida

Thermodynamically controlled regioselective glycosylation of fully unprotected sugars through Bis(boronate) intermediates

Fully unprotected D-glucose, D-mannose, and D-fructose were regioselectively glycosylated with several phenylthioglycosides to afford glycosyl-β(1→6)-α/β-D-glucopyranose, glycosyl- β(1→1)-α-D-mannofuranoside, and glycosyl-β(1→1)- β-D-fructopyranose in goo