methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate

Base Information

• Chemical Name: methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate
• CAS No.: 93292-47-8
• Molecular Formula: C₂₇H₃₈O₅Si
• Molecular Weight: 470.681
• Mol file: 93292-47-8.mol

Synonyms:methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate

Chemical Property of methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate

There total 7 articles about methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate 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: 77.0%

methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-(isopropylidenedioxy)-5(Z)-decenoate (93292-45-6) → methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate (93292-47-8)

Guidance literature:

With aq. acid;

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>-9,10-dihydroxy-5(Z)-decenoate (93292-47-8)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1021/jo00375a009

Reference yield:

2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose (93292-42-3) → methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-dihydroxy-5(Z)-decenoate (93292-47-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / tetrahydrofuran / 1.) -78 deg C, 30 min, 2.) RT, 30 min;

2: 100 percent / methanol; diethyl ether / 0.17 h / Ambient temperature

3: 65 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 6 h / Ambient temperature

With trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; water;

DOI:10.1021/jo00375a009

upstream raw materials:

methyl 8(S)-<(tert-butyldiphenylsilyl)oxy>-9,10-(isopropylidenedioxy)-5(Z)-decenoate

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

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

(Z)-(S)-8-(tert-Butyl-diphenyl-silanyloxy)-8-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oct-5-enoic acid

Downstream raw materials:

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

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

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

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