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

Base Information

• Chemical Name: 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
• CAS No.: 617715-17-0
• Molecular Formula: C₄₃H₆₄O₈Si
• Molecular Weight: 737.062

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 14 articles about 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 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: 56.0%

acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4R,6R)-4-(tertbutyldiphenylsilanyloxy)-6-(2-oxoethyl)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 (617715-17-0)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; acetonitrile; tert-butyl alcohol; at 0 ℃; for 0.5h;

DOI:10.1016/j.tet.2011.05.020

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) → 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 (617715-17-0)

Guidance literature:

Multi-step reaction with 14 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

9.1: 75 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

10.1: (S)-2-methyloxazaborolidine; borane-tetrahydrofuran complex / -10 °C

11.1: 97 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

12.1: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer; 2-methyl-propan-2-ol / 1.5 h / pH 7

13.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

14.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; Schwartz's reagent; borane-THF; (R)-2-methyl-oxazaborolidine; 2-methyl-but-2-ene; (-)-N-methylephedrine; L-Selectride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N-phenylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; phosphate buffer; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 3.1: Terashima reduction / 7.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation / 10.1: Corey-Bakshi-Shibata borohydride reduction / 13.1: Dess-Martin oxidation;

DOI:10.1002/anie.200351817

Reference yield:

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 (617715-14-7) → 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 (617715-17-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

2.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 20 °C

2.2: dimethylzinc / CH₂Cl₂ / -78 °C

2.3: 87 percent / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: 75 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

4.1: (S)-2-methyloxazaborolidine; borane-tetrahydrofuran complex / -10 °C

5.1: 97 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

6.1: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer; 2-methyl-propan-2-ol / 1.5 h / pH 7

7.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

8.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.75 h / 0 °C

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; Schwartz's reagent; borane-THF; (R)-2-methyl-oxazaborolidine; 2-methyl-but-2-ene; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; water; tert-butyl alcohol; 1.1: Dess-Martin oxidation / 3.1: Dess-Martin oxidation / 4.1: Corey-Bakshi-Shibata borohydride reduction / 7.1: Dess-Martin oxidation;

DOI:10.1002/anie.200351817

upstream raw materials:

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

(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

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

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