(-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Base Information

Chemical Name:(-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane
CAS No.:113033-00-4
Molecular Formula:C₂₂H₃₃NO₄S
Molecular Weight:407.574
Hs Code.:

Synonyms:(-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

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Chemical Property of (-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Chemical Property:

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Technology Process of (-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

There total 5 articles about (-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane 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:

: 113033-06-0
(1S,2R,3S,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-hydroxy-6,6-dimethylbicyclo<3.1.1>heptane

: 113033-00-4
(-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Guidance literature:: Multi-step reaction with 4 steps

1: DEAD, Ph₃P / benzene / 3 h / Ambient temperature

2: NaN₃ / hexamethylphosphoric acid triamide / 2 h / 50 °C

3: LiAlH₄ / diethyl ether / 0 deg C, then reflux, 1 h

4: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With lithium aluminium tetrahydride; sodium azide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; benzene;
DOI:10.1248/cpb.37.948

Reference yield:

: 103080-37-1
(1S,2R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-oxo-6,6-dimethylbicyclo<3.1.1>heptane

: 113033-00-4
(-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaOMe, 2.) NaBH₄ / 1.) MeOH, 2 h, room t., 2.) MeOH, 18 h

2: DEAD, Ph₃P / benzene / 3 h / Ambient temperature

3: NaN₃ / hexamethylphosphoric acid triamide / 2 h / 50 °C

4: LiAlH₄ / diethyl ether / 0 deg C, then reflux, 1 h

5: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With sodium tetrahydroborate; lithium aluminium tetrahydride; sodium azide; sodium methylate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; benzene;
DOI:10.1248/cpb.37.948

Reference yield:

: 82402-33-3,103080-39-3,113033-07-1,124264-29-5,124264-36-4
Methanesulfonic acid (1S,2R,3S,5R)-6,6-dimethyl-2-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-bicyclo[3.1.1]hept-3-yl ester

: 113033-00-4
(-)-(1S,2R,3R,5R)-2-<2-(tetrahydropyran-2-yloxy)ethyl>-3-benzenesulfonylamino-6,6-dimethylbicyclo<3.1.1>heptane

Guidance literature:: Multi-step reaction with 3 steps

1: NaN₃ / hexamethylphosphoric acid triamide / 2 h / 50 °C

2: LiAlH₄ / diethyl ether / 0 deg C, then reflux, 1 h

3: Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

With lithium aluminium tetrahydride; sodium azide; triethylamine; In N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;
DOI:10.1248/cpb.37.948