(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

Base Information

Chemical Name:(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester
CAS No.:691869-41-7
Molecular Formula:C₄₈H₈₃O₁₂PSi
Molecular Weight:911.239
Hs Code.:

(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

Synonyms:(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

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Chemical Property of (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

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Technology Process of (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

There total 26 articles about (Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl 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: 88.0%

: 691869-52-0
(diethoxy-phosphoryl)-acetic acid 10-(3,4-bis-triethylsilanyloxy-cyclopentyl)-1-[2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-9-triethylsilanyloxy-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

: 691869-41-7
(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 3h;
DOI:10.1021/ol049701h

Reference yield:

: 58794-19-7
3-allyl-hex-5-enal

: 691869-41-7
(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: dibutylboron triflate; Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 88 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: 91 percent / Grubb's catalyst / 1,2-dichloro-ethane / 0.33 h / 20 °C

4.1: 87 percent / 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O / 18 h / 20 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 0 °C

6.1: 58 percent / LiBH₄ / tetrahydrofuran; methanol / 24 h / 20 °C

7.1: 98 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 24 h / 20 °C

8.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 16 h / 20 °C

9.1: LiHMDS / tetrahydrofuran / 0.67 h / -78 °C

9.2: 80 percent / tetrahydrofuran / -78 - 20 °C

10.1: 99 percent / DIBAl-H / CH₂Cl₂; hexane / 1.5 h / -78 °C

11.1: 90 percent / pyridine / tetrahydrofuran / 0.5 h / 0 - 20 °C

12.1: 88 percent / acetic acid / tetrahydrofuran; H₂O / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetone; 1.1: Evans aldol reaction / 1.2: Evans aldol reaction / 3.1: ring-closing metathesis / 7.1: Mitsunobu reaction;
DOI:10.1021/ol049701h

Reference yield:

: 691869-47-3
(S)-3-((2S,3R)-5-Allyl-3-hydroxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

: 691869-41-7
(Diethoxy-phosphoryl)-acetic acid (4E,6E)-(1S,3S,8R,9R)-10-((1S,3R,4S)-3,4-dihydroxy-cyclopentyl)-9-hydroxy-1-[(E)-(1S,2R)-2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: 91 percent / Grubb's catalyst / 1,2-dichloro-ethane / 0.33 h / 20 °C

3.1: 87 percent / 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O / 18 h / 20 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 0 °C

5.1: 58 percent / LiBH₄ / tetrahydrofuran; methanol / 24 h / 20 °C

6.1: 98 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 24 h / 20 °C

7.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 16 h / 20 °C

8.1: LiHMDS / tetrahydrofuran / 0.67 h / -78 °C

8.2: 80 percent / tetrahydrofuran / -78 - 20 °C

9.1: 99 percent / DIBAl-H / CH₂Cl₂; hexane / 1.5 h / -78 °C

10.1: 90 percent / pyridine / tetrahydrofuran / 0.5 h / 0 - 20 °C

11.1: 88 percent / acetic acid / tetrahydrofuran; H₂O / 3 h / 20 °C

With pyridine; 2,6-dimethylpyridine; osmium(VIII) oxide; lithium borohydride; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetone; 2.1: ring-closing metathesis / 6.1: Mitsunobu reaction;
DOI:10.1021/ol049701h