Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside

Base Information

• Chemical Name: Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside
• CAS No.: 55722-49-1
• Molecular Formula: C16H24 O9 S
• Molecular Weight: 392.427
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID30441927
• Nikkaji Number: J313.426A
• Wikidata: Q72477433
• Mol file: 55722-49-1.mol

Synonyms:55722-49-1;Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside;ethyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside;Ethyl 2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside;[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-ethylsulfanyloxan-2-yl]methyl acetate;(2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(ethylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate;SCHEMBL3821203;DTXSID30441927;YPNFVZQPWZMHIF-CWVYHPPDSA-N;MFCD00233283;AKOS015919043;CS-0357161;W-200991;W-203104;1-(Ethylthio)-1-deoxy-beta-D-galactopyranose tetraacetate;a-D-Galactopyranoside,ethyl1-thio-,2,3,4,6-tetraacetate;Ethyl 2,3,4,6-tetra-o-acetyl-beta-D-thiogalactopyranoside;[(2R,3S,4S,5R,6S)-3,4,5-TRIS(ACETYLOXY)-6-(ETHYLSULFANYL)OXAN-2-YL]METHYL ACETATE

Chemical Property of Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside

Chemical Property:

• Melting Point: 75oC
• Boiling Point: 453oC
• Flash Point: 213oC
• PSA: 139.73000
• Density: 1.27
• LogP: 0.82260
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 392.11410351
• Heavy Atom Count: 26
• Complexity: 536

Purity/Quality:

98% ^*data from raw suppliers

Ethyl 2,3,4,6-tetra-O-acetyl-b-D-thiogalactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSC1C(C(C(C(O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CCS[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside

There total 95 articles about Ethyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside 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: 100.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + ethyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (127753-95-1) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; at -10 ℃;

DOI:10.1039/a909218h

Reference yield: 96.0%

acetyl chloride (75-36-5) + ethyl 1-thio-β-D-glucopyranoside (7473-36-1,13533-58-9,36400-88-1,56245-60-4,73494-52-7,73804-33-8,128946-17-8,686299-00-3) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

With aluminum oxide; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.carres.2005.11.035

Reference yield: 92.0%

D-Glucose (2280-44-6) + acetic anhydride (108-24-7) + ethanethiol (75-08-1) → ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5)

Guidance literature:

D-Glucose; acetic anhydride; With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

With hydrogen bromide; In acetic acid; at 0 - 20 ℃;

ethanethiol; With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200500646

upstream raw materials:

ethanethiol

β-D-mannopyranose pentaacetate

per-O-acetyl-α-D-mannopyranose

tri-n-butyltin(SC₂H₅)

Downstream raw materials:

ethyl 1-thio-α-D-mannopyranoside

methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside

Methyl 4-O-benzoyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside

Refernces

• 1、 -. "Beta-D-glucose short-chain fatty acid ester compound as well as preparation method and application thereof". Paragraph 0033; 0057; 0059. . Retrieved 2021/04/03.
• 2、 Alex, Catherine,Demchenko, Alexei V.,Visansirikul, Satsawat. "A versatile approach to the synthesis of mannosamine glycosides". . p. 6682 - 6695. Retrieved 2020/10/02.