499-23-0

Basic information

• Product Name: B,B-TREHALOSE
• Synonyms: B,B-TREHALOSE;BETA,BETATREHALOSE;SS,SSTREHALOSE;Isotrehalose, β-D-Glucopyranosyl β-D-glucopyranoside
• CAS NO: 499-23-0
• Molecular Formula: C₁₂H₂₂O₁₁
• Molecular Weight: 342.295
• Mol File: 499-23-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 130-135 °C
• Boiling Point: 675.4±55.0 °C(Predicted)
• Appearance: /
• Density: 1.76±0.1 g/cm3(Predicted)
• PKA: 12.53±0.70(Predicted)
• CAS DataBase Reference: B,B-TREHALOSE(CAS DataBase Reference)
• NIST Chemistry Reference: B,B-TREHALOSE(499-23-0)
• EPA Substance Registry System: B,B-TREHALOSE(499-23-0)

Safety Data

• Hazardous Substances Data: 499-23-0(Hazardous Substances Data)

Usage

Uses

β,β-Trehalose is a disaccharide composed of two α-glucose units. It is used in the synthesis of water-soluble bisphosphinite chiral ligands which can be used as asymmetrical hydrogenation catalysts for dehydroamino acids and their esters.

Upstream product

• 55676-46-5 2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 25018-28-4 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 108811-30-9 6-O-(triphenylmethyl)-β-D-glucopyranosyl-6'-O-(triphenylmethyl)-β-D-glucopyranoside 
• 55676-46-5 2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside 
• 502-73-8 palmitone 
• 76054-91-6 Hexadecanoic acid (2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 

Relevant articles and documents

Novel Water-Soluble Bisphosphinite Chiral Ligands Derived from α,α- And β,β-Trehalose. Application to Asymmetric Hydrogenation of Dehydroamino Acids and Their Esters in Water or an Aqueous/ Organic Biphasic Medium

Novel 2,3:4,6-di-O-isopropylidene-α-D-glucopyranosyl-(1,1)-4,6-O-isopropylidene- 2,3-di-O-diphenylphosphino-α-D-glucopyranoside (2), 2,3:4,6-di-O-cyclohexylidene-α-D-glucopyranosyl-(1,1)-4,6-O- cyclohexylidene-2,3-di-O-diphenylphosphino-α-D-glucopyranoside (4), and 2,3:4,6-di-O-cyclohexylidene-β-D-glucopyranosyl-(1,1)-4,6-O- cyclohexylidene-2,3-di-O-diphenylphosphino-β-D-glucopyranoside (11) were prepared from the corresponding α,α- or β,β-trehalose. The ligands were transformed into cationic Rh complexes, such as [Rh(α-D-glucopyranosyl-(1,1)-2,3-di-O-diphenylphosphino-α-D- glucopyranoside)(cod)]BF4 (3) and [Rh(β-D-glucopyranosyl-(1,1)-2,3-di-O-diphenylphosphino-β-D- glucopyranoside)(cod)]BF4 (12) bearing free hydroxy groups. These complexes were soluble in water and were efficient catalysts for the asymmetric hydrogenation of dehydroamino acids and their esters in water or an aqueous/organic biphasic medium with high enantioselectivity (up to 99.9% ee). Aqueous biphasic systems offer an easy separation of the aqueous catalyst phase from the product phase and allow recycling of the catalyst phase without the loss of enantioselectivity.

Synthesis and glycosylation shift of 1,1'-disaccharides

Nineteen kinds of nonreducing 1,1'-disaccharides have synthesized by modified Koenigs-Knorr method, and characterized by NMR. The glycosylation shift of each anomeric carbon has been estimated.

A NOVEL OBSERVATION ON KOENIGS-KNORR CONDENSATION OF 2,3,4,6-TETRA-O-ACETYL-α-D-GLUCOPYRANOSYL BROMIDE WITH METHYL 4,6-O-BENZYLIDENE-α-D-GLUCOPYRANOSIDE

As a result of condensation between methyl 4,6-O-benzylidene-α-D-glucopyranoside and bromo-2,3,4,6-tetra-O-acetyl-α-D-glucopyranose in 1,2-dichloroethane in presence of silver carbonate, after removal of functional groups, the following substances were ob