(1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol

Base Information

Chemical Name:(1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol
CAS No.:129368-29-2
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

Synonyms:(1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol

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Chemical Property of (1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol

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Technology Process of (1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol

There total 9 articles about (1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol 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: 83.0%

: 129368-27-0
C₂₂H₂₈O₅

: 129368-29-2
(1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at -10 ℃;
DOI:10.1016/0040-4039(90)80020-M

Reference yield:

: 699-13-8
(tetrahydropyranyloxy)acetaldehyde

: 129368-29-2
(1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol

Guidance literature:: Multi-step reaction with 5 steps

1: 1) LDA / 2) THF, HMPA, -78 deg C

2: Et₃N / CH₂Cl₂ / -10 °C

3: DBU / benzene / 50 °C

4: 1) Et₂O, CH₂Cl₂, 0 deg C 2) irradiation, benzophenone, -70 deg C, PhCH₃

5: 83 percent / LiAlH₄ / diethyl ether / -10 °C

With lithium aluminium tetrahydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In diethyl ether; dichloromethane; benzene;
DOI:10.1016/0040-4039(90)80020-M

Reference yield:

: 126958-23-4,127061-40-9,129444-45-7
(3aR,6aS)-2-Ethoxy-hexahydro-cyclopenta[b]furan-5-one

: 129368-29-2
(1S,2S,4S)-4-Benzyloxy-2-[(1R,2R)-1-hydroxymethyl-2-(tetrahydro-pyran-2-yloxymethyl)-cyclopropyl]-cyclopentanol

Guidance literature:: Multi-step reaction with 9 steps

1: NaBH₄ / methanol / 0 °C

2: NaH / tetrahydrofuran; dimethylformamide / Ambient temperature

3: 1N HCl / 1,2-dimethoxy-ethane / Ambient temperature

4: Jones reagent / acetone / 0 °C

5: 1) LDA / 2) THF, HMPA, -78 deg C

6: Et₃N / CH₂Cl₂ / -10 °C

7: DBU / benzene / 50 °C

8: 1) Et₂O, CH₂Cl₂, 0 deg C 2) irradiation, benzophenone, -70 deg C, PhCH₃

9: 83 percent / LiAlH₄ / diethyl ether / -10 °C

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/0040-4039(90)80020-M