(1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

Base Information

Chemical Name:(1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate
CAS No.:1447701-14-5
Molecular Formula:C₄₆H₅₁NO₁₈S
Molecular Weight:937.973
Hs Code.:

(1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

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Chemical Property of (1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

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Technology Process of (1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

There total 2 articles about (1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate 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:

: C₂₇H₄₂NO₁₄P

: 1447700-84-6
(2S,3R,4S,5R,6R)-6-((benzyloxy)methyl)-4,5-dihydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-3-yl benzoate

: 1447701-14-5
(1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

: (1S,2R)-1-((3aR,4R,6R,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

Guidance literature:: C₂₇H₄₂NO₁₄P; (2S,3R,4S,5R,6R)-6-((benzyloxy)methyl)-4,5-dihydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-3-yl benzoate; In dichloromethane; at 25 ℃; for 2h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2h; Overall yield = 65 %; Overall yield = 0.87 g; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja403609x

Reference yield:

: 220645-55-6
p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 1447701-14-5
(1S,2R)-1-((3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

: (1S,2R)-1-((3aR,4R,6R,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2,3-triyl triacetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: trifluorormethanesulfonic acid; triethylsilane / dichloromethane / 1 h / -78 °C / Molecular sieve

2.1: dichloromethane / 2 h / 25 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / -78 °C / Molecular sieve; Inert atmosphere

With triethylsilane; trifluorormethanesulfonic acid; In dichloromethane;
DOI:10.1021/ja403609x