(-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran
• CAS No.: 869336-51-6
• Molecular Formula: C₃₇H₅₈O₅Si₂
• Molecular Weight: 639.036
• Mol file: 869336-51-6.mol

Synonyms:(-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran

Chemical Property of (-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran

There total 3 articles about (-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran 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:

acetic acid 3-(9-bora-bicyclo[3.3.1]non-9-yl)-propyl ester (157123-07-4) + (-)-(2R,4S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-iodo-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-47-0) → (-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-51-6)

Guidance literature:

With sodium hydroxide; Pd(ppf)Cl₂; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ja055033z

Reference yield:

(-)-(2R,4S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(tributylstannyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran → (-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-51-6)

Guidance literature:

Multi-step reaction with 2 steps

1: iodine / CH₂Cl₂

2: Pd(ppf)Cl₂; aq. NaOH / tetrahydrofuran / 1 h / 20 °C

With sodium hydroxide; Pd(ppf)Cl₂; iodine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja055033z

Reference yield:

Allyl acetate (591-87-7) → (-)-(2R,4S)-6-(4'-acetoxypropyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-51-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran / 3 h / 20 °C

1.2: aq. NaOH / tetrahydrofuran / 0.5 h / 20 °C

2.1: Pd(ppf)Cl₂; aq. NaOH / tetrahydrofuran / 1 h / 20 °C

With sodium hydroxide; Pd(ppf)Cl₂; In tetrahydrofuran;

DOI:10.1021/ja055033z

upstream raw materials:

acetic acid 3-(9-bora-bicyclo[3.3.1]non-9-yl)-propyl ester

(-)-(2R,4S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-iodo-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran

Allyl acetate

Downstream raw materials:

(-)-(2R,4S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(3-hydroxypropyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran