methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate

Base Information

• Chemical Name: methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate
• CAS No.: 93292-51-4
• Molecular Formula: C₂₈H₃₆O₄Si
• Molecular Weight: 464.677

Synonyms:methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate

Chemical Property of methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate

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Technology Process of methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate

There total 16 articles about methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate 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: 81.0%

methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9-oxo-5(Z)-nonenoate (93292-49-0) + (triphenylphosphoranylidene)acetaldehyde (2136-75-6) → methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate (93292-51-4)

Guidance literature:

DOI:10.1016/0040-4039(84)80003-9

Reference yield:

(Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-8-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid (93292-43-4) → methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate (93292-51-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / methanol; diethyl ether / 0.17 h / Ambient temperature

2: 65 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 6 h / Ambient temperature

3: sodium periodate / acetone; H₂O; tetrahydrofuran / 0.25 h / Ambient temperature

4: benzene / 9 h / 80 °C

With sodium periodate; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; water; acetone; benzene;

DOI:10.1021/jo00375a009

Reference yield:

methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate (93292-47-8) → methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-11-oxo-5(Z),9(E)-undecadienoate (93292-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium periodate / acetone; H₂O; tetrahydrofuran / 0.25 h / Ambient temperature

2: benzene / 9 h / 80 °C

With sodium periodate; In tetrahydrofuran; water; acetone; benzene;

DOI:10.1021/jo00375a009

upstream raw materials:

methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9-oxo-5(Z)-nonenoate

(triphenylphosphoranylidene)acetaldehyde

Lithium; 5-(triphenyl-λ⁵-phosphanylidene)-pentanoate

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose

Downstream raw materials:

(5Z,9E,11Z,13E)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

(5Z,9E,11E,13E)-(8S,15S)-8,15-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-5,9,11,13-tetraenoic acid methyl ester

methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),9(E),11(Z),14(Z)-eicosatetraenoate

(5Z,9E,11E)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-13-hydroxy-trideca-5,9,11-trienoic acid methyl ester

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