(1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester
CAS No.:118419-09-3
Molecular Formula:C₄₁H₅₂O₇Si
Molecular Weight:684.945
Hs Code.:

(1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Chemical Property of (1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

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Technology Process of (1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

There total 11 articles about (1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-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:

: 118419-08-2
(2E,8E,10E)-(5S,6R,7R)-6-Benzyloxy-14-(tert-butyl-diphenyl-silanyloxy)-7-methoxymethoxy-5-methyl-4-oxo-tetradeca-2,8,10-trienoic acid methyl ester

: 118419-10-6
(1S,2R,4aS,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

: 118419-11-7
(1R,2R,4aS,5R,6R,7S,8aR)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

: 118419-09-3
(1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: With 2-Sulfanylpyridine; In dichloromethane; at 23 ℃; for 18h; Yield given. Yields of byproduct given;
DOI:10.1021/jo00265a036

Reference yield:

: 118419-23-1,118490-93-0
(R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-methoxymethoxy-2-methyl-hex-5-en-3-ol

: 118419-09-3
(1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: NaH, nBu₄NI / tetrahydrofuran

2: nBu₄NF / tetrahydrofuran

3: pyridine

4: 1.) ozone, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) 2 h

6: 1.) I₂, 2.) LAH / 1.) hexane, 2.) THF, 0 deg C

7: DMSO, (COCl)2 / CH₂Cl₂ / 0.17 h / -78 °C

8: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) 10 min

9: PCC, K₂HPO₄, 4-Angstroem mol. sieves / CH₂Cl₂

10: 1.) LiCl, diisopropylethyl amine, 2.) 2-mercaptopyridine / 1.) CH₃CN, 5 min, 2.) CH₂Cl₂, 23 deg C, 2 h

11: mercaptopyridine / CH₂Cl₂ / 18 h / 23 °C

With pyridine; 2-Sulfanylpyridine; dipotassium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; 4 A molecular sieve; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00265a036

Reference yield:

: (R)-3-Benzyloxy-4-methoxymethoxy-2-methyl-hex-5-en-1-ol

: 118419-09-3
(1S,2S,4aR,5R,6R,7S,8aS)-6-Benzyloxy-2-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-5-methoxymethoxy-7-methyl-8-oxo-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: pyridine

2: 1.) ozone, 2.) Me₂S / 1.) methanol, -78 deg C, 2.) 2 h

4: 1.) I₂, 2.) LAH / 1.) hexane, 2.) THF, 0 deg C

5: DMSO, (COCl)2 / CH₂Cl₂ / 0.17 h / -78 °C

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) 10 min

7: PCC, K₂HPO₄, 4-Angstroem mol. sieves / CH₂Cl₂

8: 1.) LiCl, diisopropylethyl amine, 2.) 2-mercaptopyridine / 1.) CH₃CN, 5 min, 2.) CH₂Cl₂, 23 deg C, 2 h

9: mercaptopyridine / CH₂Cl₂ / 18 h / 23 °C

With pyridine; 2-Sulfanylpyridine; dipotassium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide; 4 A molecular sieve; iodine; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium chloride; In dichloromethane;
DOI:10.1021/jo00265a036