2,2,2-trichloroethyl N-[(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]carbamate

Base Information

• Chemical Name: 2,2,2-trichloroethyl N-[(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]carbamate
• CAS No.: 868230-98-2
• Molecular Formula: C15H18 Cl3 N O6 S
• Molecular Weight: 446.736
• DSSTox Substance ID: DTXSID90693682
• Wikidata: Q82622693
• Mol file: 868230-98-2.mol

Synonyms:868230-98-2;2,2,2-trichloroethyl N-[(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]carbamate;Phenyl 2-Deoxy-1-thio-2-(2,2,2-trichloroethoxyformamido)-beta-D-galactopyranoside;DTXSID90693682;P1643;Phenyl 2-deoxy-1-thio-2-{[(2,2,2-trichloroethoxy)carbonyl]amino}-alpha-L-allopyranoside

Chemical Property of 2,2,2-trichloroethyl N-[(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]carbamate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.639
• Boiling Point: 628.852°C at 760 mmHg
• Flash Point: 334.118°C
• PSA: 137.04000
• Density: 1.598g/cm³
• LogP: 1.88710
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 444.992042
• Heavy Atom Count: 26
• Complexity: 463

Purity/Quality:

97% ^*data from raw suppliers

PHENYL 2-DEOXY-1-THIO-2-(2,2,2-TRICHLOROETHOXYFORMAMIDO)-BETA-D-GALACTOPYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)SC2C(C(C(C(O2)CO)O)O)NC(=O)OCC(Cl)(Cl)Cl
• Isomeric SMILES: C1=CC=C(C=C1)S[C@H]2[C@H]([C@H]([C@H]([C@@H](O2)CO)O)O)NC(=O)OCC(Cl)(Cl)Cl

Technology Process of 2,2,2-trichloroethyl N-[(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]carbamate

There total 1 articles about 2,2,2-trichloroethyl N-[(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylsulfanyloxan-3-yl]carbamate 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%

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside (278784-83-1) → phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside (868230-98-2)

Guidance literature:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside; With sodium methylate; In methanol; at 20 ℃; for 3h;

In methanol;

DOI:10.1016/j.cclet.2017.06.010

Reference yield: 93.0%

di-tert-butylsilyl bis(trifluoromethanesulfonate) (85272-31-7) + phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside (868230-98-2) → phenyl 2-deoxy-4,6-O-di-tert-butylsilylene-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside (868230-99-3)

Guidance literature:

With pyridine; at 20 ℃; for 0.0833333h;

DOI:10.1021/ol051592z

Reference yield: 90.0%

4-t-butylbenzaldehyde dimethyl acetal (3395-82-2) + phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside (868230-98-2) + 2,2,2-Trichloroethyl chloroformate (17341-93-4) → phenyl 4,6-O-p-tert-butylbenzylidene-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbamoyl)-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-galactopyranoside

Guidance literature:

4-t-butylbenzaldehyde dimethyl acetal; phenyl 2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside; With camphor-10-sulfonic acid; In tetrahydrofuran; acetonitrile; at 0 - 20 ℃; for 2.5h; Inert atmosphere;

2,2,2-Trichloroethyl chloroformate; With pyridine; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/acs.orglett.9b01372

upstream raw materials:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2',2',2'-trichloroethoxycarbonylamino)-β-D-galactopyranoside

Downstream raw materials:

phenyl 2-deoxy-4,6-O-di-tert-butylsilylene-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-galactopyranoside

phenyl 2-deoxy-4,6-O-di-tert-butylsilylene-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranoside

C₆₅H₈₁Cl₃N₂O₂₆SSi

phenyl 2-acetamido-3-O-acetyl-2-deoxy-4,6-O-di-tert-butylsilylene-β-D-galactopyranoside