(2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol

Base Information

Chemical Name:(2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol
CAS No.:263138-31-4
Molecular Formula:C₄₄H₆₄O₈Si
Molecular Weight:749.073
Hs Code.:

Synonyms:(2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol

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Chemical Property of (2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol

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Technology Process of (2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol

There total 14 articles about (2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol 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: 91.0%

: 263138-32-5
(2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-7-(4-nitrobenzoyl)-2,4,8,10-tetramethyl-5-hexyne

: 263138-31-4
(2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; for 1.5h;
DOI:10.1021/jo991689x

Reference yield: 43.0%

: 263138-27-8
(2R,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)hexanal

: 263138-29-0
(2R,3S,4S)-(tert-butyldiphenylsilyl)oxy-2,4-dimethyl-3-(methoxymethoxy)-5-hexyne

: 263138-30-3
(2R,3S,4S,7R,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,3,8,10-tetramethyl-5-dodecyn-7-ol

: 263138-31-4
(2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol

Guidance literature:: (2R,3S,4S)-(tert-butyldiphenylsilyl)oxy-2,4-dimethyl-3-(methoxymethoxy)-5-hexyne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -40 ℃;

(2R,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)hexanal; With lithium bromide; In tetrahydrofuran; hexane; at -35 ℃; for 1h; Further stages.;
DOI:10.1021/jo991689x

Reference yield:

: 263138-21-2
(2S,3R,4R)-(+)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol

: 263138-31-4
(2R,3S,4S,7S,8R,9R,10R)-3,9-bis(methoxymethoxy)-1-(tert-butyldiphenylsilyl)oxy-12-(4-methoxybenzyloxy)-2,4,8,10-tetramethyl-5-dodecyn-7-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 96 percent / i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 48 h / 20 °C

2.1: (c-C₆H₁₁)2BH / 1,2-dimethoxy-ethane / 6.5 h / 20 °C

2.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

3.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

4.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

5.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

6.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h

7.1: BuLi / tetrahydrofuran; hexane / -78 - -40 °C

7.2: 43 percent / LiBr / tetrahydrofuran; hexane / 1 h / -35 °C

8.1: 59 percent / i-PrO₂CN=NCO₂-i-Pr; Ph₃P / benzene / 18 h / 20 °C

9.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h

With n-butyllithium; 15-crown-5; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; benzene; 1.1: Etherification / 2.1: Addition / 2.2: Oxidation / 3.1: Reduction / 4.1: Etherification / 5.1: Hydrolysis / 6.1: Oxidation / 7.1: Metallation / 7.2: Addition / 8.1: Esterification / 9.1: Hydrolysis;
DOI:10.1021/jo991689x