(1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester
CAS No.:860799-80-0
Molecular Formula:C₄₁H₅₈O₁₂Si
Molecular Weight:770.99
Hs Code.:

(1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Synonyms:(1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

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Chemical Property of (1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

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Technology Process of (1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

There total 13 articles about (1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-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,2R,4S,4aS,5S,6R,8aR)-6-Benzyloxy-5-benzyloxymethyl-2,4-dihydroxy-1-hydroxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

: 108-24-7
acetic anhydride

: 860799-80-0
(1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 25 ℃; for 6h;
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

: 860799-80-0
(1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 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

8.1: 87 percent / aq. tert-butyl hydroperoxide; triton B / tetrahydrofuran / 16 h / 25 °C

9.1: 91 percent / (PhSe)2; NaBH₄ / ethanol / 0.5 h / 25 °C

10.1: 63 percent / NaBH₄ / methanol; CH₂Cl₂ / 24 h / 25 °C

11.1: TBAF / tetrahydrofuran / 1 h / 0 - 25 °C

12.1: Et₃N; DMAP / CH₂Cl₂ / 6 h / 25 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; oxalyl dichloride; triethylsilyl chloride; diphenyl diselenide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; methanol; ethanol; 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

: 860799-80-0
(1S,2R,4S,4aS,5S,6R,8aR)-2,4-Diacetoxy-1-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-4a-(2-trimethylsilanyl-ethoxymethoxymethyl)-decahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

4: 87 percent / aq. tert-butyl hydroperoxide; triton B / tetrahydrofuran / 16 h / 25 °C

5: 91 percent / (PhSe)2; NaBH₄ / ethanol / 0.5 h / 25 °C

6: 63 percent / NaBH₄ / methanol; CH₂Cl₂ / 24 h / 25 °C

7: TBAF / tetrahydrofuran / 1 h / 0 - 25 °C

8: Et₃N; DMAP / CH₂Cl₂ / 6 h / 25 °C

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; diphenyl diselenide; tetrabutyl ammonium fluoride; N-benzyl-trimethylammonium hydroxide; triethylamine; lithium hexamethyldisilazane; ytterbium(III) triflate; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Mander carboxylation;
DOI:10.1002/anie.200500216