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

Base Information

• Chemical Name: (2R,5R,4'S,6'R,7'S)-2-benzyloxymethyl-2-methyl-5-[4'-benzyloxy-4'-methyl-6'-hydroxy-7'-dimethylphenylsilanyl-8'-ene-1'-one-1'-yl]-tetrahydrofuran
• CAS No.: 349583-78-4
• Molecular Formula: C₃₈H₅₀O₅Si
• Molecular Weight: 614.897

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (2R,5R,4'S,6'R,7'S)-2-benzyloxymethyl-2-methyl-5-[4'-benzyloxy-4'-methyl-6'-hydroxy-7'-dimethylphenylsilanyl-8'-ene-1'-one-1'-yl]-tetrahydrofuran 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:

1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-7-dimethyl-phenyl-silanyl-non-8-ene-6-ol → (2R,5R,4'S,6'R,7'S)-2-benzyloxymethyl-2-methyl-5-[4'-benzyloxy-4'-methyl-6'-hydroxy-7'-dimethylphenylsilanyl-8'-ene-1'-one-1'-yl]-tetrahydrofuran (349583-78-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 36.5 h / 23 °C

2: 66 percent / SnCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

3: DIBAL-H / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

4: 82 percent / NaH / tetrabutylammonium iodide / tetrahydrofuran; various solvent(s) / 19 h / Heating

5: 99 percent / KOt-Bu; 18-crown-6; TBAF*3H₂O / dimethylsulfoxide; H₂O / 84 h / 85 °C

6: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7: 814 mg / toluene / -78 °C

With dmap; oxalyl dichloride; 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; 6: Swern oxidation;

DOI:10.1021/ol0160250

Reference yield:

(2S,3S)-2,3-epoxygeraniol (82188-73-6) → (2R,5R,4'S,6'R,7'S)-2-benzyloxymethyl-2-methyl-5-[4'-benzyloxy-4'-methyl-6'-hydroxy-7'-dimethylphenylsilanyl-8'-ene-1'-one-1'-yl]-tetrahydrofuran (349583-78-4)

Guidance literature:

Multi-step reaction with 13 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

8.1: 66 percent / SnCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

9.1: DIBAL-H / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

10.1: 82 percent / NaH / tetrabutylammonium iodide / tetrahydrofuran; various solvent(s) / 19 h / Heating

11.1: 99 percent / KOt-Bu; 18-crown-6; TBAF*3H₂O / dimethylsulfoxide; H₂O / 84 h / 85 °C

12.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

13.1: 814 mg / toluene / -78 °C

With dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone; toluene; benzene; 12.1: Swern oxidation;

DOI:10.1021/ol0160250

Reference yield:

(3S)-3,7-dimethyl-oct-6-ene-1,3-diol (123748-58-3) → (2R,5R,4'S,6'R,7'S)-2-benzyloxymethyl-2-methyl-5-[4'-benzyloxy-4'-methyl-6'-hydroxy-7'-dimethylphenylsilanyl-8'-ene-1'-one-1'-yl]-tetrahydrofuran (349583-78-4)

Guidance literature:

Multi-step reaction with 12 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

7.1: 66 percent / SnCl₄ / CH₂Cl₂ / 0.17 h / -78 °C

8.1: DIBAL-H / tetrahydrofuran; various solvent(s) / 0.5 h / 0 °C

9.1: 82 percent / NaH / tetrabutylammonium iodide / tetrahydrofuran; various solvent(s) / 19 h / Heating

10.1: 99 percent / KOt-Bu; 18-crown-6; TBAF*3H₂O / dimethylsulfoxide; H₂O / 84 h / 85 °C

11.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

12.1: 814 mg / toluene / -78 °C

With dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; acetone; toluene; benzene; 11.1: Swern oxidation;

DOI:10.1021/ol0160250

upstream raw materials:

diisopropyl 3-[(E)-γ-(dimethylphenylsilyl)]allyl-1,3,2-dioxaborolane-4,5-dicarboxylate

(S)-3-Benzyloxy-6-((2R,5R)-5-benzyloxymethyl-5-methyl-tetrahydro-furan-2-yl)-3-methyl-6-oxo-hexanal

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

benzyl bromide

Downstream raw materials:

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

(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,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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