(E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol

Base Information

• Chemical Name: (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol
• CAS No.: 617715-15-8
• Molecular Formula: C₄₉H₇₂O₇Si
• Molecular Weight: 801.192

Synonyms:(E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol

Chemical Property of (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol

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Technology Process of (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol

There total 8 articles about (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol 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: 87.0%

4-methylpentyne (7154-75-8) + 2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]acetaldehyde (617714-99-5) → (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol (617715-15-8)

Guidance literature:

4-methylpentyne; With Schwartz's reagent; In dichloromethane; at 20 ℃;

With dimethyl zinc(II); In dichloromethane; at -78 ℃;

2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]acetaldehyde; In dichloromethane; at -78 - 0 ℃; for 1h;

DOI:10.1002/anie.200351817

Reference yield:

(2R,6S)-2-[(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-oxodecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-4-one (617714-97-3) → (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol (617715-15-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 84 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 1.5 h / -78 °C

2.1: 73 percent / imidazole / dimethylformamide / 40 h

3.1: 95 percent / LiAlH₄; (-)-N-methylephedrine; N-ethylaniline / diethyl ether / 2 h / -78 °C

4.1: 100 percent / pyridine / CH₂Cl₂

5.1: 84 percent / HF*pyridine; pyridine / tetrahydrofuran

6.1: 73 percent / sodium hydride / benzene / 16 h / 60 °C

7.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

8.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 20 °C

8.2: dimethylzinc / CH₂Cl₂ / -78 °C

8.3: 87 percent / CH₂Cl₂ / 1 h / -78 - 0 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; Schwartz's reagent; (-)-N-methylephedrine; L-Selectride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N-phenylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Terashima reduction / 7.1: Dess-Martin oxidation;

DOI:10.1002/anie.200351817

Reference yield:

(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-1-{(2S,4S,6S)-4-hydroxy-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl}-2-methoxy-5-methyldecan-4-one (617715-10-3) → (E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol (617715-15-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 73 percent / imidazole / dimethylformamide / 40 h

2.1: 95 percent / LiAlH₄; (-)-N-methylephedrine; N-ethylaniline / diethyl ether / 2 h / -78 °C

3.1: 100 percent / pyridine / CH₂Cl₂

4.1: 84 percent / HF*pyridine; pyridine / tetrahydrofuran

5.1: 73 percent / sodium hydride / benzene / 16 h / 60 °C

6.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

7.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 20 °C

7.2: dimethylzinc / CH₂Cl₂ / -78 °C

7.3: 87 percent / CH₂Cl₂ / 1 h / -78 - 0 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; Schwartz's reagent; (-)-N-methylephedrine; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N-phenylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 2.1: Terashima reduction / 6.1: Dess-Martin oxidation;

DOI:10.1002/anie.200351817

upstream raw materials:

4-methylpentyne

2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]acetaldehyde

(2R,6S)-2-[(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-oxodecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-4-one

2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-ethanol

Downstream raw materials:

(1R,3S,5R,7R,9R,13R,15S,18S)-7-(tert-butyldiphenylsilanyloxy)-3-methoxy-18-methyl-13-((E)-4-methylpent-1-enyl)-12,19,20-trioxatricyclo[13.3.1.1^5,9]icosan-11-one

[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

2-((2R,4R,6R)-6-((S)-3-((2R,3S,6S)-6-((R,E)-2-acetoxy-6-methylhept-3-enyl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl)-4-(tert-butyldiphenylsilyloxy)tetrahydro-2H-pyran-2-yl)acetic acid

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