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

Base Information

Chemical Name:Thiocarbonic acid O-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-4-yl] ester O-pentafluorophenyl ester
CAS No.:283587-81-5
Molecular Formula:C₆₂H₆₇F₅O₁₁S
Molecular Weight:1115.27
Hs Code.:

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

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

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

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

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

: 135192-53-9
pentafluorophenoxythiocarbonyl chloride

: 283587-79-1
octyl 2,4-di-O-benzyl-α-L-fucopyranosyl-(1->2)-3,4,6-tri-O-benzyl-β-D-galactopyranoside

: 283587-81-5
Thiocarbonic acid O-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-4-yl] ester O-pentafluorophenyl ester

Guidance literature:: With dmap; In dichloromethane; for 14h;
DOI:10.1016/S0008-6215(00)00003-3

Reference yield:

: 111-87-5
octanol

: 283587-81-5
Thiocarbonic acid O-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-4-yl] ester O-pentafluorophenyl ester

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: 92 percent / NaOMe / methanol

5: 98 percent / DMAP / CH₂Cl₂ / 14 h

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:

: 127501-41-1
ethyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside

: 283587-81-5
Thiocarbonic acid O-[(2S,3S,4R,5R,6S)-3,5-bis-benzyloxy-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yloxy)-6-methyl-tetrahydro-pyran-4-yl] ester O-pentafluorophenyl ester

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: 600 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: 92 percent / NaOMe / methanol

9: 98 percent / DMAP / CH₂Cl₂ / 14 h

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