<2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester

Base Information

• Chemical Name: <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester
• CAS No.: 152453-80-0
• Molecular Formula: C₃₇H₄₂INO₄SSi
• Molecular Weight: 751.801
• Mol file: 152453-80-0.mol

Synonyms:<2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester

Chemical Property of <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester

There total 12 articles about <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester 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: 89.0%

2,2'-dipyridyldisulphide (2127-03-9) + <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (152453-79-7) → <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester (152453-80-0)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; for 15h; Ambient temperature;

DOI:10.1021/ja00136a025

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester (152453-80-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) NaH / 1.) DMF, RT, 3 h, 2.) DMF, RT, 45 min

2: 77 percent / CaCO₃, HgCl₂ / acetonitrile; H₂O / 0.83 h / Ambient temperature

3: 1.) BF₃*Et₂O, 2.) a) 3 M aq. NaOH, b) 30percent aq. H₂O₂ / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, a) from -78 deg C to RT

4: 84 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

5: 1.) Sudan III, oxygen-ozone, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT

6: aq. NaH₂PO₄, aq. NaClO₂ / acetonitrile; dimethylsulfoxide / 2 h / Ambient temperature

7: 87 percent / diethyl ether / 0.25 h / 0 °C

8: 97 percent / CuCl₂*2H₂O / methanol / 1 h / Heating

9: Pb(OAc)4 / tetrahydrofuran / 0.67 h / 0 °C

10: CrCl₂ / tetrahydrofuran / 1 h / sonication

11: 75 percent / LiOH / tetrahydrofuran; H₂O; methanol / 12 h / Ambient temperature

12: 89 percent / Ph₃P / tetrahydrofuran / 15 h / Ambient temperature

With 1H-imidazole; chromium dichloride; lead(IV) acetate; lithium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; dimethylsulfide; oil scarlet; boron trifluoride diethyl etherate; dihydrogen peroxide; oxygen; sodium hydride; ozone; triphenylphosphine; calcium carbonate; mercury dichloride; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00136a025

Reference yield:

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose (152453-72-0) → <2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid (S)-2-pyridinyl ester (152453-80-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) BF₃*Et₂O, 2.) a) 3 M aq. NaOH, b) 30percent aq. H₂O₂ / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, a) from -78 deg C to RT

2: 84 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

3: 1.) Sudan III, oxygen-ozone, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) CH₂Cl₂, MeOH, from -78 deg C to RT

4: aq. NaH₂PO₄, aq. NaClO₂ / acetonitrile; dimethylsulfoxide / 2 h / Ambient temperature

5: 87 percent / diethyl ether / 0.25 h / 0 °C

6: 97 percent / CuCl₂*2H₂O / methanol / 1 h / Heating

7: Pb(OAc)4 / tetrahydrofuran / 0.67 h / 0 °C

8: CrCl₂ / tetrahydrofuran / 1 h / sonication

9: 75 percent / LiOH / tetrahydrofuran; H₂O; methanol / 12 h / Ambient temperature

10: 89 percent / Ph₃P / tetrahydrofuran / 15 h / Ambient temperature

With 1H-imidazole; chromium dichloride; lead(IV) acetate; lithium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; dimethylsulfide; oil scarlet; boron trifluoride diethyl etherate; dihydrogen peroxide; oxygen; ozone; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00136a025

upstream raw materials:

2,2'-dipyridyldisulphide

<2R-(2R*,3R*,5S*,6E)>-3-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl-6-heptenoic acid

p-Methoxybenzyl bromide

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose

Downstream raw materials:

<4R-<4α(2E,4E),4aβ,7α(2S*,3E),8β,8aβ>>-1H-imidazole-1-carboxylic acid 5--3-butenyl>-4a,8-dimethyl-2,5-dioxo-2H,5H-pyrano<3,4-e>-1,3-oxazin-4-yl>-4-methyl-2,4-pentadienyl ester

<3S-<3α(1R*,2R*,3S*,5R*,6E),4β(1E,3E)>>-1-<(1,1-dimethylethyl)dimethylsilyl>-4-<5-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-1,3-pentadienyl>-3-<3-<<(1,1-diphenylethyl)dimethylsilyl>oxy>-1-hydroxy-7-iodo-5-<(4-methoxyphenyl)methoxy>-2-methyl..>.

Refernces