Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester

Base Information

• Chemical Name: Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester
• CAS No.: 869382-47-8
• Molecular Formula: C₄₂H₇₆O₉Si₂
• Molecular Weight: 781.231

Synonyms:Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester

Chemical Property of Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester

There total 20 articles about Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl 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:

(S)-2-Methoxy-5-methyl-hex-4-enal (869382-33-2) → Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester (869382-47-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 79 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

3.1: catecholborane; RhCl(PPh₃)3 / tetrahydrofuran

3.2: aq. H₂O₂; NaOH / tetrahydrofuran

4.1: Et₃N; DMAP / CH₂Cl₂

5.1: O₃ / CH₂Cl₂ / -78 °C

5.2: Me₂S / CH₂Cl₂

6.1: 88 percent / aq. Ba(OH)2 / tetrahydrofuran

7.1: 94 percent / PPTS / 0 °C

8.1: 95 percent / lutidine / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; dmap; barium dihydroxide; RhCl(PPh₃)3; lutidine; pyridinium p-toluenesulfonate; titanium tetrachloride; ozone; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; 6.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ja0549289

Reference yield:

(S)-2-Methoxy-5-methyl-hex-4-en-1-ol → Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester (869382-47-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 99 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 25 °C

2.1: 79 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / -78 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

4.1: catecholborane; RhCl(PPh₃)3 / tetrahydrofuran

4.2: aq. H₂O₂; NaOH / tetrahydrofuran

5.1: Et₃N; DMAP / CH₂Cl₂

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: Me₂S / CH₂Cl₂

7.1: 88 percent / aq. Ba(OH)2 / tetrahydrofuran

8.1: 94 percent / PPTS / 0 °C

9.1: 95 percent / lutidine / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; dmap; barium dihydroxide; oxalyl dichloride; RhCl(PPh₃)3; lutidine; pyridinium p-toluenesulfonate; titanium tetrachloride; ozone; dimethyl sulfoxide; triethylamine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 7.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ja0549289

Reference yield:

((R)-1-Methoxymethyl-but-3-enyloxymethyl)-benzene → Acetic acid (E)-(4S,5S)-8-[(2S,3R,4S,5S,6R)-6-((R)-2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-oct-7-enyl ester (869382-47-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: OsO₄; NMO / tetrahydrofuran; H₂O / 15 h

1.2: 60 percent / aq. NaIO₄ / tetrahydrofuran

2.1: TiCl₄ / CH₂Cl₂ / 0.33 h / cooling

2.2: (-)-sparteine / CH₂Cl₂ / 0.33 h / cooling

2.3: 90 percent / CH₂Cl₂; 1-methyl-pyrrolidin-2-one / 14 h / -30 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

4.1: 86 percent / i-Bu₂AlH / CH₂Cl₂; heptane / -78 °C

5.1: TiCl₄ / CH₂Cl₂ / 0.33 h / cooling

5.2: i-Pr₂NEt / CH₂Cl₂ / 0.33 h / cooling

5.3: 62 percent / CH₂Cl₂ / 13 h / -30 °C

6.1: 79 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

7.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7.2: 96 percent / tetrahydrofuran; hexane / 2 h / -78 °C

8.1: 88 percent / aq. Ba(OH)2 / tetrahydrofuran

9.1: 94 percent / PPTS / 0 °C

10.1: 95 percent / lutidine / CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; dmap; barium dihydroxide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; lutidine; pyridinium p-toluenesulfonate; titanium tetrachloride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; n-heptane; dichloromethane; water; 8.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/ja0549289

upstream raw materials:

(S)-2-Methoxy-5-methyl-hex-4-enal

(4S,5S)-5-Methoxy-8-methyl-nona-1,7-dien-4-ol

((1S,2S)-1-Allyl-2-methoxy-5-methyl-hex-4-enyloxy)-tert-butyl-dimethyl-silane

Acetic acid (4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-7-oxo-heptyl ester

Downstream raw materials:

acetic acid 6-{5-[6-(2-benzyloxy-3-methoxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl]-2-oxo-[1,3]dioxolan-4-yl}-4-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-hexyl ester

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