(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

Base Information

Chemical Name:(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
CAS No.:349583-75-1
Molecular Formula:C₄₇H₇₆O₅Si₃
Molecular Weight:805.374
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 10 articles about (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 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: 82.0%

: 100-39-0
benzyl bromide

: 349583-84-2
(2R,4R,5R,6'R,3'S)-2-hydroxymethyl-2-methyl-4-dimethylphenylsilanyl-5-[6'-triethylsilanyloxy-3'-benzyloxy-3'-methyl-1'-tert-butyldimethylsilanyloxy-hex-6'-yl]-tetrahydrofuran

: 349583-75-1
(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

Guidance literature:: With sodium hydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 19h; Heating;
DOI:10.1021/ol0160250

Reference yield:

: 1-tert-butyldimethylsilanyloxy-3-benzyloxy-3-methyl-7-dimethyl-phenyl-silanyl-non-8-ene-6-ol

: 349583-75-1
(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

Guidance literature:: Multi-step reaction with 4 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

With dmap; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; triethylamine; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol0160250

Reference yield:

: 82188-73-6
(2S,3S)-2,3-epoxygeraniol

: 349583-75-1
(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

Guidance literature:: Multi-step reaction with 10 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

With dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; potassium tert-butylate; pyridinium p-toluenesulfonate; tin(IV) chloride; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; acetone; benzene;
DOI:10.1021/ol0160250