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

Base Information

• Chemical Name: (2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol
• CAS No.: 250346-36-2
• Molecular Formula: C₃₃H₄₄O₈Si
• Molecular Weight: 596.793
• Mol file: 250346-36-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-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: 47.0%

(2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate (250346-47-5) → (2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol (250346-36-2)

Guidance literature:

With potassium tert-butylate; guanidine hydrochloride; In ethanol; at 20 ℃; for 0.0833333h;

DOI:10.1039/a909243i

Reference yield: 41.0%

acetic anhydride (108-24-7) + (2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol (250346-46-4) → (2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol (250346-36-2) + (2'R,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-3-hydroxy-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthyl acetate (250346-47-5) + (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:

(2'S,3'R,5'R)-2-[5-(tert-Butyldimethylsilyloxy)-1,3-dihydroxy-2-(phenylmethoxy)hexyl]-4,8-dimethoxy-1-naphthol (250346-44-2) → (2'R,3'R,5'R)-2-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-4,8-dimethoxy-1-naphthol (250346-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / manganese dioxide / CH₂Cl₂

2: 41 percent / triethylamine

With manganese(IV) oxide; triethylamine; In dichloromethane;

DOI:10.1021/ol991020c

upstream raw materials:

acetic anhydride

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

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

Benzyloxyacetyl chloride

Downstream raw materials:

C₃₂H₄₀O₈Si

(2'R,3'R,5'R)-6-[3-Acetoxy-5-(tert-butyldimethylsilyloxy)-2-(phenylmethoxy)hexanoyl]-9,9a-dihydro-5-hydroxy-4-methoxyfuro[3,2-b]naphtho[2,1-d]furan-8-(6bH)-one