(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

Base Information

Chemical Name:(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate
CAS No.:100806-47-1
Molecular Formula:C₂₃H₂₆O₆S
Molecular Weight:430.522
Hs Code.:

Synonyms:(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

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Chemical Property of (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

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Technology Process of (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

There total 8 articles about (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate 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: 82.0%

: 89291-76-9
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol

: 98-59-9
p-toluenesulfonyl chloride

: 100806-47-1
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 25 ℃; for 20h;
DOI:10.1016/S0040-4039(00)89219-9

Reference yield:

: 30725-00-9
2,3-O-isopropylidene-D-ribonic-γ-lactone

: 100806-47-1
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) RT, overnight

2: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) from -70 deg C to RT, 2 h

3: 95 percent / CH₃ONa / methanol / 24 h / Ambient temperature

4: 80 percent / CrO₃, pyridine / CH₂Cl₂ / 1 h / 14 - 25 °C

5: 42 percent / K₂CO₃, 18-crown-6 / benzene / 0.67 h / 56 °C

6: 97 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.17 h / 0 - 5 °C

7: Et₃N / CH₂Cl₂ / 17 h / Ambient temperature

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; sodium methylate; sodium hydride; potassium carbonate; triethylamine; In methanol; dichloromethane; benzene;
DOI:10.1021/jo00259a019

Reference yield:

: 100-39-0
benzyl bromide

: 100806-47-1
(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, 0 deg C, 15 min, 2.) RT, overnight

2: 1.) n-BuLi / 1.) THF, hexane, -70 deg C, 0.5 h, 2.) from -70 deg C to RT, 2 h

3: 95 percent / CH₃ONa / methanol / 24 h / Ambient temperature

4: 80 percent / CrO₃, pyridine / CH₂Cl₂ / 1 h / 14 - 25 °C

5: 42 percent / K₂CO₃, 18-crown-6 / benzene / 0.67 h / 56 °C

6: 97 percent / NaBH₄, CeCl₃*7H₂O / methanol / 0.17 h / 0 - 5 °C

7: Et₃N / CH₂Cl₂ / 17 h / Ambient temperature

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; sodium methylate; sodium hydride; potassium carbonate; triethylamine; In methanol; dichloromethane; benzene;
DOI:10.1021/jo00259a019