(2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester

Base Information

• Chemical Name: (2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester
• CAS No.: 933466-33-2
• Molecular Formula: C₃₅H₄₉NO₈
• Molecular Weight: 611.776

Synonyms:(2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester

Chemical Property of (2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester

There total 24 articles about (2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl 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: 78.0%

(3-{4-[6-(10-hydroxy-8-methoxy-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-2,5-dimethoxy-phenyl)-carbamic acid allyl ester (933466-32-1) → (2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester (933466-33-2)

Guidance literature:

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In acetone; at 20 ℃; for 1h;

DOI:10.1055/s-2006-958967

Reference yield:

2-{(4S,5S,6R)-6-[(Z)-3-(tert-butyldiphenylsiloxy)-1-methylprop-1-enyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethanal (933466-20-7) → (2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester (933466-33-2)

Guidance literature:

Multi-step reaction with 16 steps

1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 96 percent / tetrahydrofuran / 12 h / -78 - -10 °C

2.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / -78 °C

3.1: 72 percent / NMO; tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

4.1: diacetone-D-glucose; LDA; Et₃N / CpTiCl₃ / diethyl ether / 12 h / -78 - -65 °C

5.1: 88 percent / Ag₂O / CH₂Cl₂ / 48 h / 20 °C

6.1: 93 percent / LiAlH₄ / diethyl ether / 3.5 h / 0 - 20 °C

7.1: 98 percent / pyridine; CH₂Cl₂ / 1.17 h / 0 - 20 °C

8.1: 94 percent / TBAF*3H₂O / tetrahydrofuran / 2 h / 20 °C

9.1: 79 percent / LiCl; 2,6-lutidine; MsCl / dimethylformamide / 1 h / 20 °C

10.1: 2,6-di-tert-butylpyridine; NaI / acetone / 1 h / 20 °C

11.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

12.1: 396 mg / Na(Hg); Na₂HPO₄ / methanol / 1 h / -10 °C

13.1: polytriphenylphosphonium bromide / methanol / 1 h / 20 °C

14.1: 60 mg / aq. K₂CO₃ / acetone / 1 h / 20 °C

15.1: 86 percent / lithium hydroxide / 120 h / 20 °C

16.1: 78 percent / NMO; tetrapropylammonium perruuthenate / acetone / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; sodium amalgam; 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; polytriphenylphosphonium bromide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; triethylamine; sodium iodide; lithium chloride; silver(l) oxide; lithium hexamethyldisilazane; lithium diisopropyl amide; cyclopentadienyl titanium(IV) trichloride; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 1.2: Horner-Wadsworth-Emmons reaction / 10.1: Finkelstein iodination;

DOI:10.1055/s-2006-958967

Reference yield:

ethyl {(4S,5S,6R)-6-[(Z)-3-(tert-butyldiphenylsiloxy)-1-methylprop-1-enyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}acetate → (2,5-dimethoxy-3-{4-[6-(8-methoxy-10-oxo-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-phenyl)-carbamic acid allyl ester (933466-33-2)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 99 percent / DIBAL-H / CH₂Cl₂; toluene / 2 h / -78 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 96 percent / tetrahydrofuran / 12 h / -78 - -10 °C

3.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / -78 °C

4.1: 72 percent / NMO; tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

5.1: diacetone-D-glucose; LDA; Et₃N / CpTiCl₃ / diethyl ether / 12 h / -78 - -65 °C

6.1: 88 percent / Ag₂O / CH₂Cl₂ / 48 h / 20 °C

7.1: 93 percent / LiAlH₄ / diethyl ether / 3.5 h / 0 - 20 °C

8.1: 98 percent / pyridine; CH₂Cl₂ / 1.17 h / 0 - 20 °C

9.1: 94 percent / TBAF*3H₂O / tetrahydrofuran / 2 h / 20 °C

10.1: 79 percent / LiCl; 2,6-lutidine; MsCl / dimethylformamide / 1 h / 20 °C

11.1: 2,6-di-tert-butylpyridine; NaI / acetone / 1 h / 20 °C

12.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

13.1: 396 mg / Na(Hg); Na₂HPO₄ / methanol / 1 h / -10 °C

14.1: polytriphenylphosphonium bromide / methanol / 1 h / 20 °C

15.1: 60 mg / aq. K₂CO₃ / acetone / 1 h / 20 °C

16.1: 86 percent / lithium hydroxide / 120 h / 20 °C

17.1: 78 percent / NMO; tetrapropylammonium perruuthenate / acetone / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; sodium amalgam; 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; polytriphenylphosphonium bromide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; methanesulfonyl chloride; triethylamine; sodium iodide; lithium chloride; silver(l) oxide; lithium hexamethyldisilazane; lithium diisopropyl amide; cyclopentadienyl titanium(IV) trichloride; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 2.2: Horner-Wadsworth-Emmons reaction / 11.1: Finkelstein iodination;

DOI:10.1055/s-2006-958967

upstream raw materials:

(3-{4-[6-(10-hydroxy-8-methoxy-deca-2,4,6-trienyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-pent-3-enyl}-2,5-dimethoxy-phenyl)-carbamic acid allyl ester

N-(tertbutyldimethylsilyl)-2,5-dimethoxy-3-[(phenylsulfonyl)methyl]aniline

2-{(4S,5S,6R)-6-[(Z)-3-(tert-butyldiphenylsiloxy)-1-methylprop-1-enyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethanal

2,2-dimethyl-propionic acid 10-[6-(3-chloro-1-methyl-propenyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methoxy-deca-4,6,8-trienyl ester

Downstream raw materials:

10-{6-[4-(3-amino-2,5-dimethoxy-phenyl)-1-methyl-but-1-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-methoxy-deca-4,6,8-trienoic acid

10-{6-[4-(3-allyloxycarbonylamino-2,5-dimethoxy-phenyl)-1-methyl-but-1-enyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-methoxy-deca-4,6,8-trienoic acid

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