4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

Base Information

• Chemical Name: 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester
• CAS No.: 370884-71-2
• Molecular Formula: C₃₇H₅₂O₁₀
• Molecular Weight: 656.814

Synonyms:4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

Chemical Property of 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

There total 34 articles about 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl 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: 94.0%

4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-4,4a,5a,6,7,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester (370884-69-8) → 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester (370884-71-2)

Guidance literature:

4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-4,4a,5a,6,7,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 0 ℃;

With dihydrogen peroxide; sodium hydrogencarbonate;

DOI:10.1016/S0040-4039(01)01205-9

Reference yield:

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester (250226-93-8) → 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester (370884-71-2)

Guidance literature:

Multi-step reaction with 33 steps

1.1: 98 percent / H₂ / 5 percent Pd/C / ethyl acetate / 10 h / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

4.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

5.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

6.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

8.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

9.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

10.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

10.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

11.1: 77 percent / KH / tetrahydrofuran / 1 h / 20 °C

12.1: 84 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 27 h / 20 °C

13.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

14.1: 91 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.5 h / 0 °C

15.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

15.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

16.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

16.2: 91 percent / tetrahydrofuran / 1 h

17.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

17.2: 84 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0.5 h

18.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

18.2: 86 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

19.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

20.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

20.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

21.1: 810 mg / TBAF / tetrahydrofuran / 16 h / 20 °C

22.1: 100 percent / 4-methylmorpholine / CH₂Cl₂ / 16 h / 30 °C

23.1: 97 percent / SmI₂; MeOH / tetrahydrofuran / 0.25 h / 0 °C

24.1: 100 percent / CH₂Cl₂ / 16 h / 25 °C

25.1: 100 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

26.1: 85 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 3.5 h / 25 °C

27.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

27.2: 74 percent / tetrahydrofuran / 1 h / 20 °C

28.1: 83 percent / camphorsulfonic acid; H₂O / acetonitrile / 1.5 h / 20 °C

29.1: NaClO₂; 2-methyl-2-butene; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 1 h / 20 °C

30.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1.5 h / 20 °C

30.2: 66 mg / DMAP / tetrahydrofuran; benzene / 0.67 h

31.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

32.1: Zn-Cu / benzene; N,N-dimethyl-acetamide / 4 h / 90 °C

32.2: 290 mg / Pd(PPh₃)4 / benzene; N,N-dimethyl-acetamide / 2 h / 20 °C

33.1: BH₃*SMe₂ / tetrahydrofuran / 1.5 h / 0 °C

33.2: 94 percent / aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 0.5 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; hydrogen; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; copper; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc; cyclohexene; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl acetamide; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 2.1: Swern oxidation / 5.1: Yamaguchi lactonization / 15.1: Swern oxidation / 16.2: Wittig reaction / 18.1: Swern oxidation / 20.1: Swern oxidation / 26.1: Swern oxidation / 27.2: Wittig reaction / 30.1: Yamaguchi lactonization;

DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (116237-17-3) → 4-[(2S,3R,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester (370884-71-2)

Guidance literature:

Multi-step reaction with 32 steps

1.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

3.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

4.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

5.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.1: 3.0 g / Et₃N; Pd(PPh₃)4 / dimethylformamide / 13 h / 20 °C

7.1: 99 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

8.1: 100 percent / KH / tetrahydrofuran / 1 h / 20 °C

9.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 0 °C

9.2: 53 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0.5 h / 20 °C

10.1: 77 percent / KH / tetrahydrofuran / 1 h / 20 °C

11.1: 84 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 27 h / 20 °C

12.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 20 °C

13.1: 91 percent / camphorsulfonic acid / methanol; CH₂Cl₂ / 1.5 h / 0 °C

14.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

14.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

15.1: NaHMDS / tetrahydrofuran / 0.17 h / 0 °C

15.2: 91 percent / tetrahydrofuran / 1 h

16.1: cyclohexene; BH₃*SMe₂ / tetrahydrofuran / 0.5 h / 0 °C

16.2: 84 percent / aq. H₂O₂; aq. NaOH / tetrahydrofuran / 0.5 h

17.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

17.2: 86 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

18.1: diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

19.1: DMSO; (COCl)2 / CH₂Cl₂ / 1.5 h / -78 °C

19.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

20.1: 810 mg / TBAF / tetrahydrofuran / 16 h / 20 °C

21.1: 100 percent / 4-methylmorpholine / CH₂Cl₂ / 16 h / 30 °C

22.1: 97 percent / SmI₂; MeOH / tetrahydrofuran / 0.25 h / 0 °C

23.1: 100 percent / CH₂Cl₂ / 16 h / 25 °C

24.1: 100 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

25.1: 85 percent / DMSO; Et₃N; SO₃*Py / CH₂Cl₂ / 3.5 h / 25 °C

26.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

26.2: 74 percent / tetrahydrofuran / 1 h / 20 °C

27.1: 83 percent / camphorsulfonic acid; H₂O / acetonitrile / 1.5 h / 20 °C

28.1: NaClO₂; 2-methyl-2-butene; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 1 h / 20 °C

29.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1.5 h / 20 °C

29.2: 66 mg / DMAP / tetrahydrofuran; benzene / 0.67 h

30.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

31.1: Zn-Cu / benzene; N,N-dimethyl-acetamide / 4 h / 90 °C

31.2: 290 mg / Pd(PPh₃)4 / benzene; N,N-dimethyl-acetamide / 2 h / 20 °C

32.1: BH₃*SMe₂ / tetrahydrofuran / 1.5 h / 0 °C

32.2: 94 percent / aq. H₂O₂; aq. NaHCO₃ / tetrahydrofuran / 0.5 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; dimethylsulfide borane complex; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; potassium hydride; potassium hexamethylsilazane; copper; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; zinc; cyclohexene; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl acetamide; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 1.1: Swern oxidation / 4.1: Yamaguchi lactonization / 14.1: Swern oxidation / 15.2: Wittig reaction / 17.1: Swern oxidation / 19.1: Swern oxidation / 25.1: Swern oxidation / 26.2: Wittig reaction / 29.1: Yamaguchi lactonization;

DOI:10.1016/S0040-4020(02)00039-X

upstream raw materials:

4-[(4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-4,4a,5a,6,7,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

p-methoxybenzyl chloride

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

Downstream raw materials:

4-[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid

4-[(2R,3S,4aR,5aS,8R,9S,10aR,11aS)-3-Hydroxy-8-(4-methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

4-[(2S,4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-3-oxo-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

4-[(2R,4aR,5aS,8R,9S,10aR,11aS)-8-(4-Methoxy-benzyloxy)-9-(4-methoxy-benzyloxymethyl)-10a,11a-dimethyl-3-oxo-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-2-yl]-butyric acid ethyl ester

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