(3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate

Base Information

Chemical Name:(3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate
CAS No.:915790-28-2
Molecular Formula:C₅₁H₈₁NO₅Si₂
Molecular Weight:844.379
Hs Code.:

Synonyms:(3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate

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Chemical Property of (3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate

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Technology Process of (3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate

There total 9 articles about (3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate 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: 69.0%

: 915790-21-5
(2R,13S)-2-(benzyloxy)-13-(tert-butyldiphenylsilyloxy)tetradecanal

: (Z)-3-(tributylstannyl)-2-((trimethylsilyl)methyl)prop-1-enyl diisopropylcarbamate

: 915790-28-2
(3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate

Guidance literature:: With tin(IV) chloride; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ol0620287

Reference yield:

: 915790-22-6
(S)-tert-butyldiphenyl(undec-10-en-2-yloxy)silane

: 915790-28-2
(3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 9-BBN-H / tetrahydrofuran / 4 h / Heating

1.2: 90 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 12 h / 20 °C

2.1: 92 percent / CBr₄; Ph₃P / CH₂Cl₂ / 24 h / 20 °C

3.1: Mg; dibromoethane / tetrahydrofuran / 4 h / Heating

3.2: CuBr*Me₂S / tetrahydrofuran / 7 h / -25 - 20 °C

4.1: 89 percent / triflic acid / CH₂Cl₂; hexane / 48 h / 20 °C

5.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

6.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: 69 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

With 9-borabicyclo[3.3.1]nonane dimer; 1,1-Dibromoethane; carbon tetrabromide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; tin(IV) chloride; Dess-Martin periodane; magnesium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0620287

Reference yield:

: 915790-23-7
(S)-10-(tert-butyldiphenylsilyloxy)undecan-1-ol

: 915790-28-2
(3R,4S,5R,16S)-5-(benzyloxy)-16-(tert-butyldiphenylsilyloxy)-4-hydroxy-2-((trimethylsilyl)methyl)heptadec-1-en-3-yl diisopropylcarbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / CBr₄; Ph₃P / CH₂Cl₂ / 24 h / 20 °C

2.1: Mg; dibromoethane / tetrahydrofuran / 4 h / Heating

2.2: CuBr*Me₂S / tetrahydrofuran / 7 h / -25 - 20 °C

3.1: 89 percent / triflic acid / CH₂Cl₂; hexane / 48 h / 20 °C

4.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

5.1: 89 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: 69 percent / SnCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

With 1,1-Dibromoethane; carbon tetrabromide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; tin(IV) chloride; Dess-Martin periodane; magnesium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0620287