(1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester
CAS No.:860799-78-6
Molecular Formula:C₄₁H₆₂O₈Si₂
Molecular Weight:739.109
Hs Code.:

(1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Synonyms:(1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Chemical Property of (1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Technology Process of (1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

There total 8 articles about (1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester 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:

: (1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-hydroxymethyl-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 860799-78-6
(1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1002/anie.200500216

Reference yield:

: (1S,2R,4aS,6S,8aR)-6-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxymethyl-8a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalen-2-ol

: 860799-78-6
(1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH; (n-Bu)4NI / tetrahydrofuran; dimethylformamide / 24 h / 25 °C

2.1: TBAF / tetrahydrofuran / 15 h / 25 °C

3.1: 89 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 25 °C

4.1: KHMDS; TESCl / tetrahydrofuran / 0.5 h / -78 °C

4.2: PhSeCl / CH₂Cl₂ / 0.5 h / -78 °C

4.3: 80 percent / aq. H₂O₂ / tetrahydrofuran / 1 h / 0 - 25 °C

5.1: 93 percent / LiHMDS / tetrahydrofuran / 6 h / -78 °C

6.1: Yb(OTf)3 / tetrahydrofuran / 2 h / 25 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; oxalyl dichloride; triethylsilyl chloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: Swern oxidation / 5.1: Mander carboxylation;
DOI:10.1002/anie.200500216

Reference yield:

: 860799-60-6
(4aS,5S,6R,8aS)-6-Benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

: 860799-78-6
(1S,4aR,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-oxo-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / LiHMDS / tetrahydrofuran / 6 h / -78 °C

2: Yb(OTf)3 / tetrahydrofuran / 2 h / 25 °C

3: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

With 2,6-dimethylpyridine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; dichloromethane; 1: Mander carboxylation;
DOI:10.1002/anie.200500216