<1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

Base Information

Chemical Name:<1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane
CAS No.:142066-66-8
Molecular Formula:C₃₃H₃₈O₄
Molecular Weight:498.662
Hs Code.:

Synonyms:<1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

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Chemical Property of <1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

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Technology Process of <1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

There total 9 articles about <1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>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: 89.0%

: 142066-63-5
<1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-<<(methylsulfonyl)oxy>methyl>-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether

: 142066-66-8
<1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 4h; Ambient temperature;
DOI:10.1021/jm00094a017

Reference yield:

: 76-83-5
trityl chloride

: 142066-66-8
<1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

2: 69 percent / 3A-molecular sieves, pyridinium dichromate / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) MeMgCl / 1.) THF, from 0 deg C to 5 deg C, 15 min, 2.) THF, -78 deg C, 15 min

4: 79 percent / 50percent aq. AcOH, Al(Hg) / tetrahydrofuran / 1 h / 20 - 30 °C

5: 71 percent / 9-borabicyclo<3.3.1>nonane (9-BBN) / tetrahydrofuran / 4 h / 0 - 5 °C

6: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / Ambient temperature

7: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

With dmap; aluminum amalgam; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; 3 A molecular sieve; tetrabutyl ammonium fluoride; methylmagnesium chloride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00094a017

Reference yield:

: 142066-52-2
<1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol

: 142066-66-8
<1S-(1α,2β,3α,4α)>-3-<(tetrahydropyranyloxy)methyl>-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

2: 69 percent / 3A-molecular sieves, pyridinium dichromate / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) MeMgCl / 1.) THF, from 0 deg C to 5 deg C, 15 min, 2.) THF, -78 deg C, 15 min

4: 79 percent / 50percent aq. AcOH, Al(Hg) / tetrahydrofuran / 1 h / 20 - 30 °C

5: 71 percent / 9-borabicyclo<3.3.1>nonane (9-BBN) / tetrahydrofuran / 4 h / 0 - 5 °C

6: 98 percent / triethylamine / CH₂Cl₂ / 0.25 h / Ambient temperature

7: 89 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

With dmap; aluminum amalgam; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; 3 A molecular sieve; tetrabutyl ammonium fluoride; methylmagnesium chloride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00094a017