methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate

Base Information

• Chemical Name: methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate
• CAS No.: 473555-50-9
• Molecular Formula: C₂₄H₃₈O₆Si
• Molecular Weight: 450.648

Synonyms:methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate

Chemical Property of methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate

Chemical Property:

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Technology Process of methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate

There total 1 articles about methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate 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: 64.0%

Methyl (R)-3-hydroxybutyrate (3976-69-0) + (4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid (294198-49-5) → methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate (473555-50-9)

Guidance literature:

With dmap; (1S)-10-camphorsulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 72h;

DOI:10.1248/cpb.50.303

Reference yield: 62.0%

methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate (473555-50-9) → (E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (R)-2-methoxycarbonyl-1-methyl-ethyl ester (473555-51-0)

Guidance literature:

With acetic acid; In tetrahydrofuran; at 80 ℃; for 12h;

DOI:10.1248/cpb.50.303

Reference yield:

methyl (3R,8R,9S)-8-benzyloxy-9-tert-butyldimethylsiloxy-3-methyl-5-oxo-4-oxadeca (6E)-enoate (473555-50-9) → methyl (3R,8R,9S,14R,15S)-8,14-dibenzyloxy-15-tert-butyldimethylsiloxy-3,9-dimethyl-5,11-dioxo-4,10-dioxadeca (6E,12E)-dienoate (473555-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / aq. AcOH / tetrahydrofuran / 12 h / 80 °C

2: 57 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 12 h / 20 °C

With dmap; (1S)-10-camphorsulfonic acid; acetic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 2: Keck condensation;

DOI:10.1248/cpb.50.303

upstream raw materials:

Methyl (R)-3-hydroxybutyrate

(4R,5S)-4-benzyloxy-5-tert-butyldimethylsilyloxy-2(E)-hexenoic acid

Downstream raw materials:

(E)-(4R,5S)-4-Benzyloxy-5-hydroxy-hex-2-enoic acid (R)-2-methoxycarbonyl-1-methyl-ethyl ester

methyl (3R,8R,9S,14R,15S)-8,14-dibenzyloxy-15-tert-butyldimethylsiloxy-3,9-dimethyl-5,11-dioxo-4,10-dioxadeca (6E,12E)-dienoate

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