Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

Base Information

Chemical Name:Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester
CAS No.:565229-96-1
Molecular Formula:C₄₆H₆₉NO₁₀
Molecular Weight:796.055
Hs Code.:

Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

Synonyms:Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

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Chemical Property of Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

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Technology Process of Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

There total 33 articles about Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-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:

: 565229-01-8
(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-methyl-hexanal

: 565229-96-1
Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

1.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

1.3: 2.29 g / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / pH 7.0

2.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / Heating

3.1: 83 percent / HF*pyridine; pyridine / methanol / 48 h / 20 °C

4.1: diisobutylaluminum hydride / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

5.1: pyridinium p-toluenesulfonate / 15 h / 20 °C

6.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

7.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

8.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

8.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

9.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

10.1: 267 mg / Dess-Martin periodinane / CH₂Cl₂

11.1: NaHMDS / tetrahydrofuran / 20 °C

11.2: tetrahydrofuran / -78 - 20 °C

12.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

13.1: Dess-Martin periodinane / CH₂Cl₂

14.1: 65 percent / tetrahydrofuran / 0 - 20 °C

15.1: CH₂Cl₂ / 20 °C

15.2: 72 percent / K₂CO₃ / methanol / 20 °C

16.1: aq. AcOH / tetrahydrofuran / 4 h / 70 °C

17.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With pyridine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 7.1: Dess-Martin oxidation / 8.2: Wittig olefination / 10.1: Dess-Martin oxidation / 11.2: Wittig olefination / 13.1: Dess-Martin oxidation / 17.1: Dess-Martin oxidation;
DOI:10.1021/jm0204136

Reference yield:

: (3R,4S,5R,6S)-6-[3-(4-Methoxy-benzyloxy)-propyl]-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-ol

: 565229-96-1
Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: pyridinium p-toluenesulfonate / 15 h / 20 °C

2.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

3.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

4.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

5.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

6.1: 267 mg / Dess-Martin periodinane / CH₂Cl₂

7.1: NaHMDS / tetrahydrofuran / 20 °C

7.2: tetrahydrofuran / -78 - 20 °C

8.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

9.1: Dess-Martin periodinane / CH₂Cl₂

10.1: 65 percent / tetrahydrofuran / 0 - 20 °C

11.1: CH₂Cl₂ / 20 °C

11.2: 72 percent / K₂CO₃ / methanol / 20 °C

12.1: aq. AcOH / tetrahydrofuran / 4 h / 70 °C

13.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 3.1: Dess-Martin oxidation / 4.2: Wittig olefination / 6.1: Dess-Martin oxidation / 7.2: Wittig olefination / 9.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation;
DOI:10.1021/jm0204136

Reference yield:

: 565229-08-5
2(R)-methoxy-6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropran

: 565229-96-1
Carbamic acid (6Z,11Z)-(1S,2S,3R,8S,9R,10S)-1-isopropyl-3,9-bis-(4-methoxy-benzyloxy)-14-((2S,3R,4S,5R)-4-methoxymethoxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-2,8,10-trimethyl-tetradeca-6,11-dienyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

2.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

3.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

3.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

4.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

5.1: 267 mg / Dess-Martin periodinane / CH₂Cl₂

6.1: NaHMDS / tetrahydrofuran / 20 °C

6.2: tetrahydrofuran / -78 - 20 °C

7.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

8.1: Dess-Martin periodinane / CH₂Cl₂

9.1: 65 percent / tetrahydrofuran / 0 - 20 °C

10.1: CH₂Cl₂ / 20 °C

10.2: 72 percent / K₂CO₃ / methanol / 20 °C

11.1: aq. AcOH / tetrahydrofuran / 4 h / 70 °C

12.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

With hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 2.1: Dess-Martin oxidation / 3.2: Wittig olefination / 5.1: Dess-Martin oxidation / 6.2: Wittig olefination / 8.1: Dess-Martin oxidation / 12.1: Dess-Martin oxidation;
DOI:10.1021/jm0204136