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

Base Information

Chemical Name:<1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-(hydroxymethyl)-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether
CAS No.:142066-62-4
Molecular Formula:C₃₉H₅₄O₅Si
Molecular Weight:630.94
Hs Code.:

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

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

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Chemical Property of <1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-(hydroxymethyl)-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether

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Technology Process of <1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-(hydroxymethyl)-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether

There total 7 articles about <1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-(hydroxymethyl)-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether 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: 71.0%

: 142066-58-8
<1S-(1α,2β,3α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-methenyl-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether

: 142066-62-4
<1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-(hydroxymethyl)-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether

Guidance literature:: With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 - 5 ℃; for 4h;
DOI:10.1021/jm00094a017

Reference yield:

: 76-83-5
trityl chloride

: 142066-62-4
<1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-(hydroxymethyl)-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether

Guidance literature:: Multi-step reaction with 5 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

With dmap; aluminum amalgam; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; 3 A molecular sieve; 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

: 142066-62-4
<1S-(1α,2β,3α,5α)>-2-<3-<(tert-butyldimethylsilyl)oxy>-5-(hydroxymethyl)-2-<(tetrahydropyranyloxy)methyl>cyclopentanyl>ethanol triphenylmethyl ether

Guidance literature:: Multi-step reaction with 5 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

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