(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

Base Information

Chemical Name:(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester
CAS No.:860799-66-2
Molecular Formula:C₃₈H₄₇BrO₁₄
Molecular Weight:807.687
Hs Code.:

(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

Synonyms:(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

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Chemical Property of (3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

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Technology Process of (3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

There total 22 articles about (3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-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: 42.0%

: 860799-58-2
(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-hydroxy-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

: 615249-05-3
(1S,4S,5R)-2-Methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-ene

: 860799-66-2
(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

: 860799-65-1
(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2R,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

Guidance literature:: (1S,4S,5R)-2-Methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-ene; With bromine; N,N-dimethyl-aniline; In pentane; at -78 ℃; for 0.166667h;

(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-hydroxy-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester; With N,N-dimethyl-aniline; In dichloromethane; at -78 - 0 ℃; for 3h;
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

: 860799-66-2
(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 22 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

13.1: 98 percent / H₂ / Pd/C / ethanol / 16 h / 25 °C / 760 Torr

14.1: 82 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 25 °C

15.1: 91 percent / DMP; NaHCO₃ / CH₂Cl₂ / 2 h / 0 - 25 °C

16.1: 80 percent / diethyl ether / 2 h / 25 °C

17.1: 97 percent / DDQ; H₂O / tetrahydrofuran / 2 h / 25 °C

18.1: 92 percent / DMP / CH₂Cl₂ / 2 h / 0 - 25 °C

19.1: NaClO₂; Na₂PO₄; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol; tetrahydrofuran / 1 h / 25 °C

20.1: HCl / ethanol; diethyl ether / 6 h / 0 - 25 °C

20.2: Ac₂O; Et₃N; DMAP / CH₂Cl₂ / 6 h / 25 °C

21.1: 51 percent / SeO₂; TBHP / CH₂Cl₂ / 6 h / 25 °C

22.1: N,N-dimethylaniline; Br₂ / pentane / 0.17 h / -78 °C

22.2: 42 percent / N,N-dimethylaniline / CH₂Cl₂ / 3 h / -78 - 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium tetrahydroborate; selenium(IV) oxide; 2-methyl-but-2-ene; oxalyl dichloride; triethylsilyl chloride; phthalic acid dimethyl ester; diphenyl diselenide; tetrabutyl ammonium fluoride; water; hydrogen; bromine; tetra-(n-butyl)ammonium iodide; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; N,N-dimethyl-aniline; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; ytterbium(III) triflate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; 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

: 860799-66-2
(3aS,5R,6aR,7S,8R,10S,10aS)-8,10-Diacetoxy-7-acetoxymethyl-5-[(1S,2S,3R,4R,5R)-3-bromo-2-methoxy-5-(4-methoxy-benzyloxy)-bicyclo[2.2.1]hept-2-yloxy]-4-methylene-3-oxo-decahydro-2-oxa-cyclopenta[d]naphthalene-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 18 steps

1.1: 93 percent / LiHMDS / tetrahydrofuran / 6 h / -78 °C

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

3.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

4.1: 87 percent / aq. tert-butyl hydroperoxide; triton B / tetrahydrofuran / 16 h / 25 °C

5.1: 91 percent / (PhSe)2; NaBH₄ / ethanol / 0.5 h / 25 °C

6.1: 63 percent / NaBH₄ / methanol; CH₂Cl₂ / 24 h / 25 °C

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

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

9.1: 98 percent / H₂ / Pd/C / ethanol / 16 h / 25 °C / 760 Torr

10.1: 82 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 25 °C

11.1: 91 percent / DMP; NaHCO₃ / CH₂Cl₂ / 2 h / 0 - 25 °C

12.1: 80 percent / diethyl ether / 2 h / 25 °C

13.1: 97 percent / DDQ; H₂O / tetrahydrofuran / 2 h / 25 °C

14.1: 92 percent / DMP / CH₂Cl₂ / 2 h / 0 - 25 °C

15.1: NaClO₂; Na₂PO₄; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol; tetrahydrofuran / 1 h / 25 °C

16.1: HCl / ethanol; diethyl ether / 6 h / 0 - 25 °C

16.2: Ac₂O; Et₃N; DMAP / CH₂Cl₂ / 6 h / 25 °C

17.1: 51 percent / SeO₂; TBHP / CH₂Cl₂ / 6 h / 25 °C

18.1: N,N-dimethylaniline; Br₂ / pentane / 0.17 h / -78 °C

18.2: 42 percent / N,N-dimethylaniline / CH₂Cl₂ / 3 h / -78 - 0 °C

With 2,6-dimethylpyridine; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium tetrahydroborate; selenium(IV) oxide; 2-methyl-but-2-ene; phthalic acid dimethyl ester; diphenyl diselenide; tetrabutyl ammonium fluoride; water; hydrogen; bromine; N-benzyl-trimethylammonium hydroxide; sodium hydrogencarbonate; N,N-dimethyl-aniline; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; ytterbium(III) triflate; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; tert-butyl alcohol; pentane; 1.1: Mander carboxylation;
DOI:10.1002/anie.200500216