(2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

Base Information

Chemical Name:(2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal
CAS No.:263138-36-9
Molecular Formula:C₃₀H₅₂O₉
Molecular Weight:556.737
Hs Code.:

Synonyms:(2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

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Chemical Property of (2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

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Technology Process of (2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

There total 16 articles about (2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal 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: 99.0%

: 263138-35-8
(2R,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecan-1-ol

: 263138-36-9
(2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; for 1h;
DOI:10.1021/jo991689x

Reference yield:

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

: 263138-36-9
(2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

Guidance literature:: Multi-step reaction with 13 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

10.1: 95 percent / TsNHNH₂; NaOAc / 1,2-dimethoxy-ethane; H₂O / Heating

11.1: 99 percent / i-PrNEt₂; Bu₄NI / CH₂Cl₂ / 42 h / 20 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

13.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

With n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; 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 / 10.1: Hydrogenation / 11.1: Etherification / 12.1: Hydrolysis / 13.1: Oxidation;
DOI:10.1021/jo991689x

Reference yield:

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

: 263138-36-9
(2S,3S,4S,7R,8S,9R,10R)-12-(4-Methoxy-benzyloxy)-3,7,9-tris-methoxymethoxy-2,4,8,10-tetramethyl-dodecanal

Guidance literature:: Multi-step reaction with 12 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

8.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1.5 h

9.1: 95 percent / TsNHNH₂; NaOAc / 1,2-dimethoxy-ethane; H₂O / Heating

10.1: 99 percent / i-PrNEt₂; Bu₄NI / CH₂Cl₂ / 42 h / 20 °C

11.1: 96 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

12.1: 99 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h

With n-butyllithium; 15-crown-5; N,N-diethyl-N-isopropylamine; di-isopropyl azodicarboxylate; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; 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 / 8.1: Hydrolysis / 9.1: Hydrogenation / 10.1: Etherification / 11.1: Hydrolysis / 12.1: Oxidation;
DOI:10.1021/jo991689x