Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

Base Information

Chemical Name:Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate
CAS No.:122519-51-1
Molecular Formula:C₄₄H₆₂O₈Si₂
Molecular Weight:775.142
Hs Code.:

Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

Synonyms:Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

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Chemical Property of Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

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Technology Process of Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

There total 24 articles about Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate 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:

: 82740-87-2
(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate

: 122519-51-1
Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

Guidance literature:: Multi-step reaction with 24 steps

1: 100 percent / K₂CO₃ / methanol / 4 h / 25 °C

2: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 3 h

3: 1.) BH₃*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 1 h, 2.) 15 min

4: 45 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h

5: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

6: 1.) BF₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 15 min

7: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 3 h

8: 86 percent / amberlyst-15 (H+) / methanol / 0.75 h / 25 °C

9: 85 percent / pyridine / 4 h / 0 °C

10: 91 percent / dimethylsulfoxide / 2 h / 70 °C

11: DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

12: 89 percent / benzene / 1 h / 25 °C

13: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) 15 min

14: 81 percent / CH₂Cl₂; toluene / 4 h / -10 °C

15: 100 percent / 1,2-dichloro-ethane / 3 h / 25 °C

16: 95 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

17: 80 percent / diethyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH / CH₂Cl₂; 1,2-dichloro-ethane / 16 h / -20 °C

18: SO₃-pyr, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

19: 1.) Ph₃P / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) -78 deg C, 20 min

20: 96 percent / n-Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

21: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 0.75 h / 0 °C

22: 100 percent / CH₂Cl₂ / 1 h / 25 °C

24: 1.) CuI / 1.) THF, -40 deg C, 45 min, 2.) -78 deg C, 1,5 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; copper(l) iodide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; Amberlyst-15 (H+); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja00199a029

Reference yield:

: 95791-07-4
(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

: 122519-51-1
Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

Guidance literature:: Multi-step reaction with 23 steps

1: 100 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 3 h

2: 1.) BH₃*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 1 h, 2.) 15 min

3: 45 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h

4: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

5: 1.) BF₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 15 min

6: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 3 h

7: 86 percent / amberlyst-15 (H+) / methanol / 0.75 h / 25 °C

8: 85 percent / pyridine / 4 h / 0 °C

9: 91 percent / dimethylsulfoxide / 2 h / 70 °C

10: DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

11: 89 percent / benzene / 1 h / 25 °C

12: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) 15 min

13: 81 percent / CH₂Cl₂; toluene / 4 h / -10 °C

14: 100 percent / 1,2-dichloro-ethane / 3 h / 25 °C

15: 95 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

16: 80 percent / diethyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH / CH₂Cl₂; 1,2-dichloro-ethane / 16 h / -20 °C

17: SO₃-pyr, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

18: 1.) Ph₃P / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) -78 deg C, 20 min

19: 96 percent / n-Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

20: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 0.75 h / 0 °C

21: 100 percent / CH₂Cl₂ / 1 h / 25 °C

23: 1.) CuI / 1.) THF, -40 deg C, 45 min, 2.) -78 deg C, 1,5 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; copper(l) iodide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; Amberlyst-15 (H+); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja00199a029

Reference yield:

: 122490-43-1
(4aR,6R,8aS)-6-Allyl-4,4a,6,8a-tetrahydro-2,2-dimethylpyrano<3,2-d>-m-dioxin

: 122519-51-1
Methyl (Z)-4,8:7,11-dianhydro-14-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-10-O-(p-methoxybenzyl)-3-methyl-8-C-methyl-5-O-(trimethylsilyl)-L-erythro-L-allo-tetradec-2-enonate

Guidance literature:: Multi-step reaction with 22 steps

1: 1.) BH₃*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 1 h, 2.) 15 min

2: 45 percent / H₂ / Pd(OH)2 / ethyl acetate / 3 h

3: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

4: 1.) BF₃*THF, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) 15 min

5: 1.) KH / 1.) THF, 0 deg C, 15 min, 2.) THF, 3 h

6: 86 percent / amberlyst-15 (H+) / methanol / 0.75 h / 25 °C

7: 85 percent / pyridine / 4 h / 0 °C

8: 91 percent / dimethylsulfoxide / 2 h / 70 °C

9: DIBAL / CH₂Cl₂ / 0.75 h / -78 °C

10: 89 percent / benzene / 1 h / 25 °C

11: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) 15 min

12: 81 percent / CH₂Cl₂; toluene / 4 h / -10 °C

13: 100 percent / 1,2-dichloro-ethane / 3 h / 25 °C

14: 95 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

15: 80 percent / diethyl L-tartrate, Ti(O-i-Pr)4, t-BuOOH / CH₂Cl₂; 1,2-dichloro-ethane / 16 h / -20 °C

16: SO₃-pyr, Et₃N / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

17: 1.) Ph₃P / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) -78 deg C, 20 min

18: 96 percent / n-Bu₄NF / tetrahydrofuran / 0.33 h / 0 °C

19: 83 percent / camphorsulfonic acid / CH₂Cl₂ / 0.75 h / 0 °C

20: 100 percent / CH₂Cl₂ / 1 h / 25 °C

22: 1.) CuI / 1.) THF, -40 deg C, 45 min, 2.) -78 deg C, 1,5 h

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; copper(l) iodide; borane-THF; 2-methyl-but-2-ene; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; Amberlyst-15 (H+); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/ja00199a029