(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

Base Information

Chemical Name:(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol
CAS No.:250346-46-4
Molecular Formula:C₃₁H₄₂O₇Si
Molecular Weight:554.756
Hs Code.:

Synonyms:(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

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Chemical Property of (2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

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Technology Process of (2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

There total 7 articles about (2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol 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: 62.0%

: 250346-44-2
(2'S,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-1,3-dihydroxy-2-(phenylmethoxy)hexyl]-4,8-dimethoxy-1-naphthol

: 250346-46-4
(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

Guidance literature:: With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1039/a909243i

Reference yield:

: 19810-31-2
Benzyloxyacetyl chloride

: 250346-46-4
(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 84 percent / n-butyllithium / -78 °C

2.1: tin(II) trifluoromethanesulfonate; triethylamine / CH₂Cl₂ / -78 °C

2.2: TMEDA / CH₂Cl₂ / cooling

3.1: 84 percent / imidazole / dimethylformamide

4.1: 82 percent / lithium borohydride / tetrahydrofuran / 0 °C

5.1: 80 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂

6.1: 44 percent / (i-PrO)TiCl₃ / CH₂Cl₂ / 0.15 h / 0 °C

7.1: 62 percent / manganese dioxide / CH₂Cl₂

With 1H-imidazole; manganese(IV) oxide; lithium borohydride; tin(II) trifluoromethanesulfonate; n-butyllithium; tetrapropylammonium perruthennate; titanium(IV) trichloride isopropoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol991020c

Reference yield:

: 137238-71-2
(4R)-3-[2-(Phenylmethoxy)acetyl]-4-(phenylmethyl)oxazolidin-2-one

: 250346-46-4
(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

Guidance literature:: Multi-step reaction with 6 steps

1.1: tin(II) trifluoromethanesulfonate; triethylamine / CH₂Cl₂ / -78 °C

1.2: TMEDA / CH₂Cl₂ / cooling

2.1: 84 percent / imidazole / dimethylformamide

3.1: 82 percent / lithium borohydride / tetrahydrofuran / 0 °C

4.1: 80 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide / CH₂Cl₂

5.1: 44 percent / (i-PrO)TiCl₃ / CH₂Cl₂ / 0.15 h / 0 °C

6.1: 62 percent / manganese dioxide / CH₂Cl₂

With 1H-imidazole; manganese(IV) oxide; lithium borohydride; tin(II) trifluoromethanesulfonate; tetrapropylammonium perruthennate; titanium(IV) trichloride isopropoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol991020c