(-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene

Base Information

Chemical Name:(-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene
CAS No.:186382-52-5
Molecular Formula:C₂₆H₂₄O₅S
Molecular Weight:448.54
Hs Code.:

Synonyms:(-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene

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Chemical Property of (-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene

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Technology Process of (-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene

There total 10 articles about (-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene 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: 86.0%

: 186382-54-7
(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2R,3R,4S,5S,6R)-3-benzenesulfonyl-5,6-bis-benzyloxy-7-oxa-bicyclo[2.2.1]hept-2-yl ester

: 186382-52-5
(-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene

Guidance literature:: With potassium carbonate; In tetrahydrofuran; at 60 ℃; for 6h;
DOI:10.1016/S0957-4166(96)00461-2

Reference yield:

: 87057-40-7
(+/-)-trans-2,3-bis(phenylsulfonyl)-7-oxabicyclo[2.2.1]hept-5-ene

: 186382-52-5
(-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene

Guidance literature:: Multi-step reaction with 6 steps

1: KOH / acetonitrile / 24 h / Ambient temperature

2: aq. OsO₄, Me₃NO / acetone; 2-methyl-propan-2-ol / 48 h

3: 89 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / Ambient temperature

4: 92 percent / aq. DDQ / CH₂Cl₂ / 24 h / Ambient temperature

5: Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

6: 86 percent / aq. K₂CO₃ / tetrahydrofuran / 6 h / 60 °C

With dmap; potassium hydroxide; osmium(VIII) oxide; trimethylamine-N-oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0957-4166(96)00461-2

Reference yield:

: (+/-)-5-exo-((p-methoxy)-benzyloxy)-6-endo-(phenylsulfonyl)-7-oxabicyclo<2.2.1>heptane-2,3-exo-diol

: 186382-52-5
(-)-(1S,4S,5R,6S)-5,6-exo-bis-(benzyloxy)-2-(phenylsulfonyl)-7-oxabicyclo<2.2.1>hept-2-ene

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / NaH, n-Bu₄NI / tetrahydrofuran / 24 h / Ambient temperature

2: 92 percent / aq. DDQ / CH₂Cl₂ / 24 h / Ambient temperature

3: Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

4: 86 percent / aq. K₂CO₃ / tetrahydrofuran / 6 h / 60 °C

With dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0957-4166(96)00461-2