2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL CYANIDE

Base Information

• Chemical Name: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL CYANIDE
• CAS No.: 52443-07-9
• Molecular Formula: C15H19NO9
• Molecular Weight: 357.317
• Mol file: 52443-07-9.mol

Synonyms:2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL CYANIDE;D-glycero-L-manno-Heptononitrile, 2,6-anhydro-, 3,4,5,7-tetraacetate;2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosylcyanide;2,3,4,6-TETRA-O-ACETYL-SS-D-GALACTOPYRANOSYL CYANIDE

Chemical Property of 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL CYANIDE

Chemical Property:

• PSA: 138.22000
• LogP: -0.36442

Purity/Quality:

98%min ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosyl cyanide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL CYANIDE

There total 25 articles about 2,3,4,6-TETRA-O-ACETYL-BETA-D-GALACTOPYRANOSYL CYANIDE 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: 93.0%

(E)-3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose oxime acetate → 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile (52443-07-9)

Guidance literature:

With sodium acetate; In acetic acid; at 100 ℃;

DOI:10.1080/07328300008544067

Reference yield: 79.0%

D-Galactose (10257-28-0) + trimethylsilyl cyanide (7677-24-9) + acetic anhydride (108-24-7) → 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile (52443-07-9)

Guidance literature:

D-Galactose; acetic anhydride; With pyridine; sodium acetate; at 100 ℃; for 2h;

trimethylsilyl cyanide; With boron trifluoride diethyl etherate; In nitromethane; at 35 ℃; for 2h;

DOI:10.1016/j.tetasy.2003.10.007

Reference yield: 78.0%

1,3,4,5-tetra-O-acetyl-2,6-anhydro-7-deoxy-7-nitro-L-glycero-L-galactoheptitol (113972-88-6) → 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile (52443-07-9)

Guidance literature:

With phosphorus trichloride; In pyridine; for 16h; 0 deg C to room temp.;

DOI:10.1016/S0008-6215(00)90894-2

upstream raw materials:

1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose

mercury(II) cyanide

benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside

1,3,4,5-tetra-O-acetyl-2,6-anhydro-7-deoxy-7-nitro-L-glycero-L-galactoheptitol

Downstream raw materials:

1,3-diphenyl-2-(tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptosyl)imidazolidine

5-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)tetrazole

2-(3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol-1-yl)-1,3-diphenylimidazolidine

3,4,5,7,-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptose tosylhydrazone

Refernces

• 1、 Coxon,B.,Fletcher,H.G.. "-". . p. 922 - 926. Retrieved 1964.
• 2、 Paloumbis, George,Petrou, Christos C.,Nock, Berthold,Maina, Theodosia,Pairas, George,Tsoungas, Petros G.,Cordopatis, Paul. "Synthesis of a protected δ-glyco-amino acid building block for incorporation into peptide chains". . p. 845 - 852. Retrieved 2008/01/06.
• 3、 Lichtenthaler, Frieder W.,Nakamura, Katsumi,Klotz, Juergen. "(-)-Daucic Acid: Revision of Configuration, Synthesis, and Biosynthetic Implications". . p. 5838 - 5843. Retrieved 2007/10/03.