(2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal

Base Information

Chemical Name:(2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal
CAS No.:475233-05-7
Molecular Formula:C₂₉H₅₄O₅Si₂
Molecular Weight:538.916
Hs Code.:

Synonyms:(2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal

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Chemical Property of (2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal

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Technology Process of (2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal

There total 10 articles about (2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal 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: 97.0%

: 475233-04-6
(2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethylheptan-1-ol

: 475233-05-7
(2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.75h;
DOI:10.1016/S0040-4020(02)00723-8

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 475233-05-7
(2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal

Guidance literature:: Multi-step reaction with 7 steps

1.1: 74 percent / i-Pr₂NEt / CH₂Cl₂ / 192 h / 20 °C

2.1: DIBAL-H / tetrahydrofuran / 0.5 h / -78 °C

3.1: NaHMDS / tetrahydrofuran; diethyl ether / 4 h / 0 °C

3.2: 0.106 g / diethyl ether; tetrahydrofuran / 0.42 h / 0 °C

4.1: 9-BBN / tetrahydrofuran / 7 h / 20 °C

4.2: 98 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / 0 °C

5.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

7.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; 3.2: Wittig reaction / 7.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(02)00723-8

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 475233-05-7
(2S,3R,4R,5R)-4-benzyloxymethoxy-2,7-bis-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-1-heptanal

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 0.271 g / KBEt₃H / diethyl ether / 0.5 h / -78 °C

2.1: 74 percent / i-Pr₂NEt / CH₂Cl₂ / 192 h / 20 °C

3.1: DIBAL-H / tetrahydrofuran / 0.5 h / -78 °C

4.1: NaHMDS / tetrahydrofuran; diethyl ether / 4 h / 0 °C

4.2: 0.106 g / diethyl ether; tetrahydrofuran / 0.42 h / 0 °C

5.1: 9-BBN / tetrahydrofuran / 7 h / 20 °C

5.2: 98 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 1 h / 0 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

7.1: 99 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

8.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

With 2,6-dimethylpyridine; 9-borabicyclo[3.3.1]nonane dimer; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1.2: Cram-Felkin-Nguyen reduction / 4.2: Wittig reaction / 8.1: Dess-Martin oxidation;
DOI:10.1016/S0040-4020(02)00723-8