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

Base Information

• Chemical Name: 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
• CAS No.: 440333-92-6
• Molecular Formula: C₃₅H₄₈O₁₀
• Molecular Weight: 628.76

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of 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

There total 37 articles about 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 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:

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 (370884-73-4) → 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 (440333-92-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 40 ℃;

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-[(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 (440333-92-6)

Guidance literature:

Multi-step reaction with 37 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

34.1: Dess-Martin periodinate; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

35.1: 113 mg / DBU / toluene / 0.5 h / 20 °C

36.1: 98 percent / NaBH₄ / methanol; CH₂Cl₂ / 2 h / -78 °C

37.1: aq. LiOH / tetrahydrofuran / 1 h / 40 °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 tetrahydroborate; 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; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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 / 34.1: Dess-Martin oxidation;

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-[(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 (440333-92-6)

Guidance literature:

Multi-step reaction with 36 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

33.1: Dess-Martin periodinate; NaHCO₃ / CH₂Cl₂ / 0.5 h / 20 °C

34.1: 113 mg / DBU / toluene / 0.5 h / 20 °C

35.1: 98 percent / NaBH₄ / methanol; CH₂Cl₂ / 2 h / -78 °C

36.1: aq. LiOH / tetrahydrofuran / 1 h / 40 °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 tetrahydroborate; 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; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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 / 33.1: Dess-Martin oxidation;

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

upstream 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 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

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