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

Base Information

Chemical Name:(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate
CAS No.:250346-47-5
Molecular Formula:C₃₃H₄₄O₈Si
Molecular Weight:596.793
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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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-naphthyl acetate

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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-naphthyl acetate

There total 8 articles about (2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate 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: 41.0%

: 108-24-7
acetic anhydride

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

: 250346-36-2
(2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol

: 250346-47-5
(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate

: (2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1039/a909243i

Reference yield:

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

: 250346-47-5
(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / manganese dioxide / CH₂Cl₂

2: 20 percent / triethylamine

With manganese(IV) oxide; triethylamine; In dichloromethane;
DOI:10.1021/ol991020c

Reference yield:

: 19810-31-2
Benzyloxyacetyl chloride

: 250346-47-5
(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate

Guidance literature:: Multi-step reaction with 8 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

8.1: 20 percent / triethylamine

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