(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

Base Information

Chemical Name:(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one
CAS No.:790662-61-2
Molecular Formula:C₃₅H₅₆O₆S₂Si
Molecular Weight:665.044
Hs Code.:

(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

Synonyms:(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

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Chemical Property of (2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

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Technology Process of (2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

There total 11 articles about (2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one 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:

: 790662-52-1
(2R,4R,5S,1'R)-[5-[1'-(tert-butyldimethylsilanyloxy)-3'-(triethylsilanyl)prop-2'-ynyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

: 790662-61-2
(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

2.1: 94 percent / NaI / acetone / 48 h / 75 °C

3.1: HMPA; t-BuLi / tetrahydrofuran / 0.75 h / -78 °C

3.2: 12 mg / t-BuOK; TBAF / dimethylsulfoxide; H₂O; tetrahydrofuran / 4 h / 95 °C

4.1: TBAF / dimethylformamide; tetrahydrofuran / 80 °C

5.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 20 °C

6.1: 97 percent / phosphate buffer; DDQ / CH₂Cl₂ / 0 - 20 °C / pH 7

7.1: iPr₂NEt; DMSO; SO₃*Pyr / CH₂Cl₂ / 0.25 h / 0 °C

8.1: 93 percent / Cy₂BCl; Et₃N / diethyl ether; hexane / 0.42 h / -78 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; phosphate buffer; pyridine-SO₃ complex; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol048381z

Reference yield:

: 790662-54-3
(S)-2-[3-(4-methoxybenzyloxy)-2-methylpropyl][1,3]dithiane

: 790662-61-2
(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: HMPA; t-BuLi / tetrahydrofuran / 0.75 h / -78 °C

1.2: 12 mg / t-BuOK; TBAF / dimethylsulfoxide; H₂O; tetrahydrofuran / 4 h / 95 °C

2.1: TBAF / dimethylformamide; tetrahydrofuran / 80 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 20 °C

4.1: 97 percent / phosphate buffer; DDQ / CH₂Cl₂ / 0 - 20 °C / pH 7

5.1: iPr₂NEt; DMSO; SO₃*Pyr / CH₂Cl₂ / 0.25 h / 0 °C

6.1: 93 percent / Cy₂BCl; Et₃N / diethyl ether; hexane / 0.42 h / -78 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; pyridine-SO₃ complex; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol048381z

Reference yield:

: 790662-50-9
(1S,2R)-{[2-(tert-butyldimethylsilanyloxy)-4-(triethylsilanyl)-1-vinylbut-3-ynyl]dimethylsilanyl}benzene

: 790662-61-2
(2R,5S,6S,2'R,5'R,1''R)-7-(2-{5'-[1''-(tert-butyldimethylsilanyloxy)prop-2''-ynyl]tetrahydrofuran-2'-ylmethyl}-[1,3]dithian-2-yl)-5-hydroxy-1-(4-methoxybenzyloxy)-2,6-dimethylheptan-3-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 62 percent / SnCl₄ / toluene; CH₂Cl₂ / 0.75 h / -78 °C

2.1: DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 2.5 h / 0 °C

3.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.75 h / 0 °C

4.1: 94 percent / NaI / acetone / 48 h / 75 °C

5.1: HMPA; t-BuLi / tetrahydrofuran / 0.75 h / -78 °C

5.2: 12 mg / t-BuOK; TBAF / dimethylsulfoxide; H₂O; tetrahydrofuran / 4 h / 95 °C

6.1: TBAF / dimethylformamide; tetrahydrofuran / 80 °C

7.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 20 °C

8.1: 97 percent / phosphate buffer; DDQ / CH₂Cl₂ / 0 - 20 °C / pH 7

9.1: iPr₂NEt; DMSO; SO₃*Pyr / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 93 percent / Cy₂BCl; Et₃N / diethyl ether; hexane / 0.42 h / -78 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; phosphate buffer; pyridine-SO₃ complex; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tin(IV) chloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1021/ol048381z