B,B-TREHALOSE

Base Information

• Chemical Name: B,B-TREHALOSE
• CAS No.: 499-23-0
• Molecular Formula: C12H22O11
• Molecular Weight: 342.3
• Mol file: 499-23-0.mol

Synonyms:3,3'-Thiodipropionyl chloride;3,3'-thiodipropionic acid dichloride;2-Carboxyethylthiopropionyl chloride;3,3'-Thiobispropanoyl chloride;Propionyl chloride,3,3'-thiodi;3,3'-Thiodipropionic acid chloride;3,3'-thiopropionyl chloride;3,3'-thiodipropanoylchloride;3,3'-Thiodipropionyl dichloride;Propanoyl chloride,3,3'-thiobis;

Chemical Property of B,B-TREHALOSE

Chemical Property:

• Melting Point: 130-135 °C
• Boiling Point: 675.4±55.0 °C(Predicted)
• PKA: 12.53±0.70(Predicted)
• PSA: 189.53000
• Density: 1.76±0.1 g/cm3(Predicted)
• LogP: -5.39720

Purity/Quality:

99%, ^*data from raw suppliers

b,b-Trehalose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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.

Technology Process of B,B-TREHALOSE

There total 14 articles about B,B-TREHALOSE which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (25018-28-4) → β,β-trehalose (499-23-0)

Guidance literature:

With hydrogen; palladium dihydroxide; In methanol; water; ethyl acetate;

DOI:10.1248/cpb.42.982

Reference yield:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3947-62-4) → β,β-trehalose (499-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: NIS, TfOH, MS 4A / CH₂Cl₂ / 0.5 h / Ambient temperature

2: NaOMe / methanol / 0.25 h / Heating

With N-iodo-succinimide; trifluorormethanesulfonic acid; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/jo990448m

Reference yield:

tetra-O-benzyl glucopyranosyl chloride (25320-59-6) → β,β-trehalose (499-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 9 percent / AgOTf, tetramethylurea, molecular sieves 4A / CH₂Cl₂ / 3 h / Ambient temperature

2: H₂ / Pd(OH)2 / methanol; ethyl acetate; H₂O

With 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; tetramethylurea; palladium dihydroxide; In methanol; dichloromethane; water; ethyl acetate;

DOI:10.1248/cpb.42.982

upstream raw materials:

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside

methyl 4,6-O-benzylidene-α-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

2,3,4,6-tetra-O-acetyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-1-β-D-glucopyranoside

6-O-(triphenylmethyl)-β-D-glucopyranosyl-6'-O-(triphenylmethyl)-β-D-glucopyranoside

palmitone

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

Refernces

• 1、 Roennow, Tor E. C. L.,Meldel, Morten,Bock, Klaus. "SYNTHESIS OF UNSYMMETRICAL TREHALOSE ANALOGUES BY SILVER TRIFLUOROMETHANESULPHONATE PROMOTED GLYCOSYLATIONS". . p. 197 - 212. Retrieved 2007/10/02.
• 2、 Parrish, Frederick W.,Meagher, Michael M.,Reilly, Peter J.. "Chromatographic procedures for isolating α,β-trehalose formed during the preparation of β,β-trehalose". . p. 129 - 135. Retrieved 2007/10/02.