C₇₂H₁₂₂O₉SSi₃

Base Information

• Chemical Name: C₇₂H₁₂₂O₉SSi₃
• CAS No.: 184291-77-8
• Molecular Formula: C₇₂H₁₂₂O₉SSi₃
• Molecular Weight: 1248.08

Synonyms:C₇₂H₁₂₂O₉SSi₃

Chemical Property of C₇₂H₁₂₂O₉SSi₃

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of C₇₂H₁₂₂O₉SSi₃

There total 32 articles about C₇₂H₁₂₂O₉SSi₃ 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:

t-butyldimethylsiyl triflate (69739-34-0) → C72H122O9SSi3 (184291-77-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 12 h

3: 1.) KHMDS, 18-crown-6 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 0 deg C, 5 h

4: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

5: 96 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

6: 90 percent / HF, pyridine / tetrahydrofuran / 9 h / Ambient temperature

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 to RT, 20 min

8: 1.) KOtBu / 1.) THF, -78 deg C, 10 min, 2.) THF, -50 deg C, 21 h

9: 91 percent / morpholine, I₂ / benzene / 22 h / 45 - 50 °C

10: 214 mg / NiCl₂, CrCl₂ / tetrahydrofuran / 23 h / Ambient temperature

11: 85 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h

12: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

13: 98 percent / DIBAL-H / CH₂Cl₂ / 0.42 h / -78 °C

14: Et₃N / CH₂Cl₂ / 1 h / 0 °C

15: LiBr / CH₂Cl₂; acetone / 0.25 h / Ambient temperature

16: LDA

With morpholine; pyridine; 2,6-dimethylpyridine; chromium dichloride; lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; hydrogen fluoride; potassium tert-butylate; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium bromide; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; benzene;

DOI:10.1021/ja961374o

Reference yield:

(2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol (106296-58-6,106357-21-5,106357-23-7,106357-22-6) → C72H122O9SSi3 (184291-77-8)

Guidance literature:

Multi-step reaction with 16 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 12 h

3: 1.) KHMDS, 18-crown-6 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 0 deg C, 5 h

4: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

5: 96 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

6: 90 percent / HF, pyridine / tetrahydrofuran / 9 h / Ambient temperature

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 to RT, 20 min

8: 1.) KOtBu / 1.) THF, -78 deg C, 10 min, 2.) THF, -50 deg C, 21 h

9: 91 percent / morpholine, I₂ / benzene / 22 h / 45 - 50 °C

10: 214 mg / NiCl₂, CrCl₂ / tetrahydrofuran / 23 h / Ambient temperature

11: 85 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h

12: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

13: 98 percent / DIBAL-H / CH₂Cl₂ / 0.42 h / -78 °C

14: Et₃N / CH₂Cl₂ / 1 h / 0 °C

15: LiBr / CH₂Cl₂; acetone / 0.25 h / Ambient temperature

16: LDA

With morpholine; pyridine; 2,6-dimethylpyridine; chromium dichloride; lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; hydrogen fluoride; potassium tert-butylate; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium bromide; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; benzene;

DOI:10.1021/ja961374o

Reference yield:

4R,6-bis(tert-butyldimethylsilanyloxy)-3S,5S-dimethylhex-1-ene (457623-10-8) → C72H122O9SSi3 (184291-77-8)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 12 h

2: 1.) KHMDS, 18-crown-6 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 0 deg C, 5 h

3: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

4: 96 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

5: 90 percent / HF, pyridine / tetrahydrofuran / 9 h / Ambient temperature

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 to RT, 20 min

7: 1.) KOtBu / 1.) THF, -78 deg C, 10 min, 2.) THF, -50 deg C, 21 h

8: 91 percent / morpholine, I₂ / benzene / 22 h / 45 - 50 °C

9: 214 mg / NiCl₂, CrCl₂ / tetrahydrofuran / 23 h / Ambient temperature

10: 85 percent / H₂ / 10percent Pd/C / ethyl acetate / 0.5 h

11: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

12: 98 percent / DIBAL-H / CH₂Cl₂ / 0.42 h / -78 °C

13: Et₃N / CH₂Cl₂ / 1 h / 0 °C

14: LiBr / CH₂Cl₂; acetone / 0.25 h / Ambient temperature

15: LDA

With morpholine; pyridine; 2,6-dimethylpyridine; chromium dichloride; lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; hydrogen fluoride; potassium tert-butylate; hydrogen; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium bromide; nickel dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone; benzene;

DOI:10.1021/ja961374o

upstream raw materials:

2,2-Dimethyl-propionic acid (5E,7Z)-(9S,10S,11R)-10-(4-methoxy-benzyloxy)-9,11-dimethyl-12-oxo-trideca-5,7-dienyl ester

t-butyldimethylsiyl triflate

p-Methoxybenzyl bromide

(2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol

Downstream raw materials:

2,2-dimethylpropanoic acid, [2S-(2α(5E,7Z,9S,10S,11R,13R,15Z,17R,18R,20Z,22R),3β,4β,5α,6β)]-18,20-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-23-(4-{[(1,1-dimethylethyl)dimethylsilyl]oxy}tetrahydro-3,5-dimethyl-6-(phenylthio)-2H-pyran-2-yl)-9,11,13,

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