(1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

Base Information

Chemical Name:(1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate
CAS No.:1447701-09-8
Molecular Formula:C₂₈H₃₁NO₁₀S
Molecular Weight:573.621
Hs Code.:

Synonyms:(1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

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Chemical Property of (1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

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Technology Process of (1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

There total 1 articles about (1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate 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: 81.0%

: 1246533-87-8
C₂₄H₂₇NO₈S

: 108-24-7
acetic anhydride

: 1447701-09-8
(1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

Guidance literature:: With pyridine; at 25 ℃; for 2h;
DOI:10.1021/ja403609x

Reference yield: 69.0%

: 1447701-09-8
(1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

: 107-66-4
dibutyl phosphate

: 1447701-11-2
(1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(dibutoxyphosphoryloxy)-6-(methoxycarbonyl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

Guidance literature:: (1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate; dibutyl phosphate; In dichloromethane; at 25 ℃; for 3h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; at 0 ℃; for 10h; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja403609x

Reference yield:

: 1447701-09-8
(1S,2R)-3-(benzyloxy)-1-((3aR,4R,6S,7aS)-6-(methoxycarbonyl)-2-oxo-6-(phenylthio)hexahydro-2H-pyrano[3,4-d]oxazol-4-yl)propane-1,2-diyl diacetate

: 1447701-15-6
(1S,2R)-1-((3aR,4R,6S,7aS)-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)-3-(benzyloxy)propane-1,2-diyl diacetate

: (1S,2R)-1-((3aR,4R,6R,7aS)-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)-3-(benzyloxy)propane-1,2-diyl diacetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dichloromethane / 3 h / 25 °C / Molecular sieve; Inert atmosphere

1.2: 10 h / 0 °C / Molecular sieve; Inert atmosphere

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

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

In dichloromethane;
DOI:10.1021/ja403609x