(7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate

Base Information

Chemical Name:(7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate
CAS No.:142581-35-9
Molecular Formula:C₂₈H₃₀O₇
Molecular Weight:478.542
Hs Code.:

Synonyms:(7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate

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Chemical Property of (7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate

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Technology Process of (7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate

There total 12 articles about (7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate 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: 47.2%

: 1486-51-7
p-(benzyloxy)benzoic acid

: 142581-33-7
endo-(7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-4-ol

: 142581-35-9
(7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 0.0833333h;
DOI:10.1021/jo00043a037

Reference yield:

: 122068-25-1,127179-63-9,127179-64-0,142694-78-8
(3aS,3bS,6aR,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-7-oxo-3a,3b,6,6a,7,7a-hexahydro-pentaleno[1,2-d][1,3]dioxole-4-carboxylic acid ethyl ester

: 142581-35-9
(7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate

Guidance literature:: Multi-step reaction with 7 steps

1: 42.7 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

2: 1.) NaH / 1.) THF, r. t., 30 min, 2.) 10 min

3: 76 percent / Bu₃SnH, AIBN / toluene / Heating

4: 85 percent / DIBAL / tetrahydrofuran / 0.33 h / -78 °C

5: 69 percent / C₅H₅N / 2 h / Ambient temperature

6: 81 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

7: DCC / CH₂Cl₂

With pyridine; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1021/jo00043a037

Reference yield:

: 142581-31-5
exo-(2S,3R)-8-(hydroxymethyl)-6β-<(tert-butyldimethylsilyl)oxy>-2,3-(isopropylidenedioxy)bicyclo<3.3.0>oct-7-ene

: 142581-35-9
(7S,8R)-2-(acetoxymethyl)-7,8-(isopropylidenedioxy)bicyclo<3.3.0>oct-2-en-exo-4-yl p-(benzyloxy)benzoate

Guidance literature:: Multi-step reaction with 3 steps

1: 69 percent / C₅H₅N / 2 h / Ambient temperature

2: 81 percent / TBAF*3H₂O / tetrahydrofuran / 1 h / Ambient temperature

3: DCC / CH₂Cl₂

With pyridine; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00043a037