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

Base Information

• Chemical Name: (+)-(2R,4R,4'S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran
• CAS No.: 869336-71-0
• Molecular Formula: C₃₇H₆₀O₄Si₂
• Molecular Weight: 625.052

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

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

Chemical Property:

Purity/Quality:

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

There total 5 articles about (+)-(2R,4R,4'S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-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: 99.0%

(+)-(2R,4R,4'S)-6-(4'-acetoxypentyl)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-57-2) → (+)-(2R,4R,4'S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-71-0)

Guidance literature:

With methanol; potassium carbonate; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ja055033z

Reference yield:

Acetic acid (S)-4-(9-bora-bicyclo[3.3.1]non-9-yl)-1-methyl-butyl ester → (+)-(2R,4R,4'S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 mg / Pd(ppf)Cl₂; aq. NaOH / tetrahydrofuran / 1 h / 20 °C

2: 99 percent / MeOH; K₂CO₃ / tetrahydrofuran / 3 h / 20 °C

With methanol; sodium hydroxide; Pd(ppf)Cl₂; potassium carbonate; In tetrahydrofuran;

DOI:10.1021/ja055033z

Reference yield:

(2R,4R)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-iodo-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran → (+)-(2R,4R,4'S)-2-[2-(tert-butyldiphenylsiloxy)ethyl]-6-(4'-hydroxypentyl)-4-(triisopropylsilyloxy)-3,4-dihydro-2H-pyran (869336-71-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 mg / Pd(ppf)Cl₂; aq. NaOH / tetrahydrofuran / 1 h / 20 °C

2: 99 percent / MeOH; K₂CO₃ / tetrahydrofuran / 3 h / 20 °C

With methanol; sodium hydroxide; Pd(ppf)Cl₂; potassium carbonate; In tetrahydrofuran;

DOI:10.1021/ja055033z

upstream raw materials:

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

(S)-4-penten-2-ol

acetic acid (S)-1-methylbut-3-enyl ester

Downstream raw materials:

(S)-5-{(1S,3R,5R,6S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-triisopropylsilanyloxy-2,7-dioxa-bicyclo[4.1.0]hept-1-yl}-pentan-2-ol

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