Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester

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Chemical Name:Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester
CAS No.:115352-45-9
Molecular Formula:C₂₅H₃₈O₈
Molecular Weight:466.572
Hs Code.:

Synonyms:Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester

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Chemical Property of Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester

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Technology Process of Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester

There total 10 articles about Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl 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: 96.0%

: 108-24-7
acetic anhydride

: 102727-59-3
(2R,5S,7R)-2-Benzyloxy-7-methyl-8-(tetrahydro-pyran-2-yloxy)-octane-1,5,7-triol

: 115352-45-9
Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester

Guidance literature:: With pyridine; Ambient temperature;
DOI:10.1016/S0040-4020(01)86915-5

Reference yield:

: 102716-68-7
(3R,6S)-3-Benzyloxy-6-((E)-3-hydroxy-2-methyl-propenyl)-tetrahydro-pyran-2-one

: 115352-45-9
Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(R)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 43 percent / diethyl (+)-tartrate, Ti(Oi-Pr)4, TBHP / CH₂Cl₂ / 48 h / -20 °C / diethyl (-)-tartrate instead of diethyl (+)-tartrate

2: PPTS / CH₂Cl₂ / 5 h

3: 85 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / Ambient temperature

4: 96 percent / pyridine / Ambient temperature

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)86915-5

Reference yield:

: 110-87-2
3,4-dihydro-2H-pyran

: 115352-45-9
Acetic acid (1S,4R)-5-acetoxy-4-benzyloxy-1-[(S)-2-hydroxy-2-methyl-3-(tetrahydro-pyran-2-yloxy)-propyl]-pentyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: PPTS / CH₂Cl₂ / 5 h

2: lithium aluminum hydride / tetrahydrofuran / 2 h / Ambient temperature

3: pyridine / Ambient temperature

With pyridine; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(01)86915-5