[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

Base Information

Chemical Name:[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester
CAS No.:74028-40-3
Molecular Formula:C₂₁H₃₀O₆
Molecular Weight:378.466
Hs Code.:

Synonyms:[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

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Chemical Property of [(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

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Technology Process of [(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

There total 1 articles about [(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl 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:

: 32233-38-8
3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether

: 74028-40-3
[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 2 N NaOH / methanol / 0.5 h / Ambient temperature

2: diethyl ether / 5 °C

With sodium hydroxide; In methanol; diethyl ether;
DOI:10.1016/0040-4020(81)80005-1

Reference yield:

: 74028-40-3
[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

: 74028-42-5
3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (β-isomer)

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) chromyl chloride / 1.) CH₂Cl₂, t-BuOH, pyridine, CCl₄, -78 deg C, 40 min (prep. of reagent), 2.) CH₂Cl₂, up to RT, then 35 deg C, 2.5 h

2: 46 percent / 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg, 20 min, 3.) THF, -78 deg C, 10 min (adding), then same temp, 2 h

3: 91 percent / H₂ / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature

4: 37 percent / 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H₂O, 175 deg C, 15 min

With n-butyllithium; potassium tert-butylate; hydrogen; chromyl chloride; diisopropylamine; palladium on activated charcoal; In ethanol;
DOI:10.1016/0040-4020(81)80005-1

Reference yield:

: 74028-40-3
[(1R,2S,3R)-2-Benzyloxymethyl-5-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

: 73996-31-3
3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (α-isomer)

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) chromyl chloride / 1.) CH₂Cl₂, t-BuOH, pyridine, CCl₄, -78 deg C, 40 min (prep. of reagent), 2.) CH₂Cl₂, up to RT, then 35 deg C, 2.5 h

2: 46 percent / 1.) diisopropylamine, n-butyllithium / 1.) THF, hexane, -78 deg C, 15 min, 2.) -78 deg, 20 min, 3.) THF, -78 deg C, 10 min (adding), then same temp, 2 h

3: 91 percent / H₂ / 5percent Pd-C / ethanol / 1.6 h / Ambient temperature

4: 1.) potassium t-butoxide / 1.) benzene, 30 deg C (adding), then 70 deg C, 4 h, 2.) HMPA-H₂O, 175 deg C, 15 min

With n-butyllithium; potassium tert-butylate; hydrogen; chromyl chloride; diisopropylamine; palladium on activated charcoal; In ethanol;
DOI:10.1016/0040-4020(81)80005-1