(3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene

Base Information

• Chemical Name: (3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene
• CAS No.: 349583-69-3
• Molecular Formula: C₃₇H₆₄O₃Si₃
• Molecular Weight: 641.17

Synonyms:(3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene

Chemical Property of (3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene

There total 7 articles about (3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene 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: 93.0%

1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-7-dimethyl-phenyl-silanyl-non-8-ene-6-ol + triethylsilyl chloride (994-30-9) → (3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene (349583-69-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 23 ℃; for 36.5h;

DOI:10.1021/ol0160250

Reference yield:

(2S,3S)-2,3-epoxygeraniol (82188-73-6) → (3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene (349583-69-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Red-Al / tetrahydrofuran / 0 °C

2.1: PPTS / benzene / Heating

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

4.1: Et₃N; DMAP

5.1: OsO₄; NMO / acetone / pH 7

5.2: Pb(OAc)4 / ethyl acetate

6.1: t-BuOK; n-BuLi / tetrahydrofuran; various solvent(s) / 0.5 h / -78 - -45 °C

6.2: tetrahydrofuran; various solvent(s) / 0.75 h / -78 °C

6.3: 77 percent / tetrahydrofuran; various solvent(s) / -78 - 23 °C

7.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 36.5 h / 23 °C

With dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; dichloromethane; acetone; benzene;

DOI:10.1021/ol0160250

Reference yield:

(3S)-3,7-dimethyl-oct-6-ene-1,3-diol (123748-58-3) → (3S,6R,7S)-1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-6-triethylsilanyloxy-7-dimethylphenylsilanyl-non-8-ene (349583-69-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: PPTS / benzene / Heating

2.1: DIBAL-H / CH₂Cl₂ / -78 °C

3.1: Et₃N; DMAP

4.1: OsO₄; NMO / acetone / pH 7

4.2: Pb(OAc)4 / ethyl acetate

5.1: t-BuOK; n-BuLi / tetrahydrofuran; various solvent(s) / 0.5 h / -78 - -45 °C

5.2: tetrahydrofuran; various solvent(s) / 0.75 h / -78 °C

5.3: 77 percent / tetrahydrofuran; various solvent(s) / -78 - 23 °C

6.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 36.5 h / 23 °C

With dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; acetone; benzene;

DOI:10.1021/ol0160250

upstream raw materials:

triethylsilyl chloride

(2S,3S)-2,3-epoxygeraniol

(3S)-3,7-dimethyl-oct-6-ene-1,3-diol

4-benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexanal

Downstream raw materials:

(2R,4R,5R,6R',3S')-[5-(6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl)-4-dimethylphenylsilanyl-2-methyltetrahydrofuran-2-yl]-formic acid methyl ester

(4S,6R,2'R,5'R,2''R,4''R,5''R)-1-[2'-methyl-2'-benzyloxymethyl-tetrahydrofuran-5'-yl]-6-[2''-methyl-2''-carbomethoxy-4''-dimethylphenylsilanyl-tetrahydrofuran-5''-yl]-4-benzyloxy-4-methyl-6-triethylsilanyloxy-hex-1-one

(2R,4R,5R,6R',3S')-2-benzyloxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

(2R,5R,4'S,6'R,7'S)-2-benzyloxymethyl-2-methyl-5-[4'-benzyloxy-4'-methyl-6'-triethylsilanyloxy-7'-dimethylphenylsilanyl-8'-ene-1'-one-1'-yl]-tetrahydrofuran

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