Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester
• CAS No.: 283587-76-8
• Molecular Formula: C₆₂H₆₇F₅O₁₁S
• Molecular Weight: 1115.27
• Mol file: 283587-76-8.mol

Synonyms:Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester

Chemical Property of Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester

There total 12 articles about Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester 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: 98.0%

pentafluorophenoxythiocarbonyl chloride (135192-53-9) + octyl 2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside (283587-74-6) → Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester (283587-76-8)

Guidance literature:

With dmap; In dichloromethane;

DOI:10.1016/S0008-6215(00)00003-3

Reference yield:

octanol (111-87-5) → Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester (283587-76-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / Hg(CN)2; molecular sieves 3 Angstroem; HgBr₂ / acetonitrile

2: 97 percent / NaOMe / methanol

3: 71 percent / DMTST; DTBMP; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h

4: 95 percent / NaOMe / methanol / 4 h / 20 °C

5: 98 percent / DMAP / CH₂Cl₂

With dmap; 2,6-di-tert-butyl-4-methylpyridine; 3 A molecular sieve; 4 A molecular sieve; sodium methylate; mercury(II) cyanide; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; mercury dibromide; In methanol; dichloromethane; acetonitrile; 1: Glycosylation / 2: Deacetylation / 3: Glycosylation / 4: Deacetylation / 5: Acylation;

DOI:10.1016/S0008-6215(00)00003-3

Reference yield:

ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside (127501-41-1) → Thiocarbonic acid O-[(2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-6-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yl] ester O-pentafluorophenyl ester (283587-76-8)

Guidance literature:

Multi-step reaction with 9 steps

1: NaOMe / methanol

2: camphorsulfonic acid

3: 93 percent / NaH / dimethylformamide

4: 84 percent / AcOH / 70 °C

5: 500 mg / Bu₄NHSO₄; NaOH / CH₂Cl₂; H₂O / 48 h / 20 °C

6: 89 percent / pyridine

7: 71 percent / DMTST; DTBMP; 4 Angstroem molecular sieves / CH₂Cl₂ / 4 h

8: 95 percent / NaOMe / methanol / 4 h / 20 °C

9: 98 percent / DMAP / CH₂Cl₂

With pyridine; dmap; sodium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; acetic acid; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Deacetylation / 2: Cyclization / 3: Alkylation / 4: Hydrolysis / 5: Alkylation / 6: Acetylation / 7: Glycosylation / 8: Deacetylation / 9: Acylation;

DOI:10.1016/S0008-6215(00)00003-3

upstream raw materials:

pentafluorophenoxythiocarbonyl chloride

octyl 2,3-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside

octanol

ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside

Downstream raw materials:

octyl 3,4,6-tri-O-benzyl-2-O-(2,3-di-O-benzyl-α-L-xylo-hexopyranosyl)-(1->2)-β-D-galactopyranoside