4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol

Base Information

• Chemical Name: 4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol
• CAS No.: 122490-71-5
• Molecular Formula: C₄₀H₅₂O₆Si
• Molecular Weight: 656.935

Synonyms:4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol

Chemical Property of 4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol

There total 28 articles about 4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol 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: 92.0%

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-L-erythro-α-L-allo-tetradec-2-enopyranol (122490-70-4,122490-80-6) → 4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol (122490-71-5)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 0.0833333h;

DOI:10.1021/ja00199a029

Reference yield:

(2R,3S,6R)-2-acetoxymethyl-6-allyl-3,6-dihydro-2H-pyran-3-yl acetate (82740-87-2) → 4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol (122490-71-5)

Guidance literature:

Multi-step reaction with 28 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

25: 100 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 25 °C

26: 95 percent / DBU / benzene / 1.5 h / 70 °C

27: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

28: 92 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 0.08 h / -10 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; triethylsilane; 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; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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:

(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (95791-07-4) → 4,8:7,11:10,14-Trianhydro-1-O-(tert-butyldiphenylsilyl)-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol (122490-71-5)

Guidance literature:

Multi-step reaction with 27 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

24: 100 percent / pyridinium p-toluenesulfonate / methanol / 1 h / 25 °C

25: 95 percent / DBU / benzene / 1.5 h / 70 °C

26: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

27: 92 percent / Et₃SiH, BF₃*Et₂O / CH₂Cl₂ / 0.08 h / -10 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; triethylsilane; 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; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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

upstream raw materials:

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-L-erythro-α-L-allo-tetradec-2-enopyranol

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

(2R,3S,6R)-6-allyl-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

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

Downstream raw materials:

4,8:7,11:10,14-Trianhydro-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enitol

4,8:7,11:10,14-Trianhydro-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-2,12-dimethyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enoic acid

3-[(2S,3R,4aS,8aS,9aR,10aR)-3-(4-Methoxy-benzyloxy)-4a,5-dimethyl-3,4,4a,7,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-2-yl]-propionic acid

Methyl 4,8:7,11:10,14-trianhydro-2,3,6,9,12,13-hexadeoxy-5-O-(p-methoxybenzyl)-12-methyl-7-C-methyl-D-erythro-D-allo-tetradec-12-enonate

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