(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

Base Information

Chemical Name:(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
CAS No.:263138-32-5
Molecular Formula:C₅₁H₆₇NO₁₁Si
Molecular Weight:898.179
Hs Code.:

(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

Synonyms:(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

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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)-7-(4-nitrobenzoyl)-2,4,8,10-tetramethyl-5-hexyne

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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)-7-(4-nitrobenzoyl)-2,4,8,10-tetramethyl-5-hexyne

There total 12 articles about (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 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: 59.0%

: 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

: 62-23-7
4-nitro-benzoic acid

: 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

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In benzene; at 20 ℃; for 18h;
DOI:10.1021/jo991689x

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

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;
DOI:10.1021/jo991689x

Reference yield:

: 263138-22-3
(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-3-methoxymethoxy-5-hexyne

: 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

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

2.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

3.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

4.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

5.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h

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

6.2: 43 percent / LiBr / tetrahydrofuran; hexane / 1 h / -35 °C

7.1: 59 percent / i-PrO₂CN=NCO₂-i-Pr; Ph₃P / benzene / 18 h / 20 °C

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; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; benzene; 1.1: Addition / 1.2: Oxidation / 2.1: Reduction / 3.1: Etherification / 4.1: Hydrolysis / 5.1: Oxidation / 6.1: Metallation / 6.2: Addition / 7.1: Esterification;
DOI:10.1021/jo991689x