2-Decanone, 10-chloro-4-hydroxy-1-[(4-methoxyphenyl)methoxy]-5-methyl-1-[(2R,3R, 4R,5R,6R)-tetrahydro-4,5-bis[(4-methoxyphenyl)methoxy]-3-methyl-6-(2 -methyl-2-propenyl)-2H-pyran-2-yl]-6-[(triethylsilyl)oxy]-, (1S,4S,5R,6R)-

Base Information

• Chemical Name: 2-Decanone, 10-chloro-4-hydroxy-1-[(4-methoxyphenyl)methoxy]-5-methyl-1-[(2R,3R, 4R,5R,6R)-tetrahydro-4,5-bis[(4-methoxyphenyl)methoxy]-3-methyl-6-(2 -methyl-2-propenyl)-2H-pyran-2-yl]-6-[(triethylsilyl)oxy]-, (1S,4S,5R,6R)-
• CAS No.: 392692-62-5
• Molecular Formula: C51H75ClO10Si
• Molecular Weight: 911.689
• Mol file: 392692-62-5.mol

Synonyms:

Chemical Property of 2-Decanone, 10-chloro-4-hydroxy-1-[(4-methoxyphenyl)methoxy]-5-methyl-1-[(2R,3R, 4R,5R,6R)-tetrahydro-4,5-bis[(4-methoxyphenyl)methoxy]-3-methyl-6-(2 -methyl-2-propenyl)-2H-pyran-2-yl]-6-[(triethylsilyl)oxy]-, (1S,4S,5R,6R)-

Chemical Property:

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Technology Process of 2-Decanone, 10-chloro-4-hydroxy-1-[(4-methoxyphenyl)methoxy]-5-methyl-1-[(2R,3R, 4R,5R,6R)-tetrahydro-4,5-bis[(4-methoxyphenyl)methoxy]-3-methyl-6-(2 -methyl-2-propenyl)-2H-pyran-2-yl]-6-[(triethylsilyl)oxy]-, (1S,4S,5R,6R)-

There total 24 articles about 2-Decanone, 10-chloro-4-hydroxy-1-[(4-methoxyphenyl)methoxy]-5-methyl-1-[(2R,3R, 4R,5R,6R)-tetrahydro-4,5-bis[(4-methoxyphenyl)methoxy]-3-methyl-6-(2 -methyl-2-propenyl)-2H-pyran-2-yl]-6-[(triethylsilyl)oxy]-, (1S,4S,5R,6R)- 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-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-propionaldehyde (194934-58-2) → (1S,4S,5R,6R)-10-chloro-4-hydroxy-1-(p-methoxybenzyloxy)-1-[4,5-(R,R)-bis(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-5-methyl-6-(triethylsiloxy)-decan-2-one (392692-62-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: LiCl; i-Pr₂NEt / acetonitrile / 0.17 h / 20 °C

1.2: 96 percent / acetonitrile / 16 h / 20 °C

2.1: 98 percent / aq. AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol / 16 h / 20 °C

3.1: 100 percent / NaHCO₃; H₂ / Pd(OH)2/C / methanol / 20 h / 20 °C

4.1: 97 percent / Ph₃CBF₄ / tetrahydrofuran / 0.5 h / 0 °C

5.1: 94 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

6.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

6.2: 96 percent / tetrahydrofuran; H₂O / 4 h / 20 °C

7.1: aq. AcOH / tetrahydrofuran / 60 h / 20 °C

7.2: KOH / methanol / 20 h / 20 °C

8.1: 81 percent / toluene; tetrahydrofuran / 2 h / 120 °C

9.1: 94 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 2 h / 20 °C

10.1: Et₃N / diethyl ether / 2.5 h / -78 °C

11.1: diethyl ether / 17 h / -78 - -20 °C

11.2: aq. H₂O₂ / methanol; various solvent(s) / 2 h / 20 °C / pH 7

With barium dihydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; hydrogen; trityl tetrafluoroborate; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 1.2: Horner-Wadsworth-Emmons chain extension / 2.1: Sharpless asymmetric dihydroxylation / 6.2: Horner-Wadsworth-Emmons chain extension / 7.1: intramolecular hetero-Michael addition;

DOI:10.1039/b504149j

Reference yield:

(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane (862509-84-0) → (1S,4S,5R,6R)-10-chloro-4-hydroxy-1-(p-methoxybenzyloxy)-1-[4,5-(R,R)-bis(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-5-methyl-6-(triethylsiloxy)-decan-2-one (392692-62-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2.1: LiCl; i-Pr₂NEt / acetonitrile / 0.17 h / 20 °C

2.2: 96 percent / acetonitrile / 16 h / 20 °C

3.1: 98 percent / aq. AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol / 16 h / 20 °C

4.1: 100 percent / NaHCO₃; H₂ / Pd(OH)2/C / methanol / 20 h / 20 °C

5.1: 97 percent / Ph₃CBF₄ / tetrahydrofuran / 0.5 h / 0 °C

6.1: 94 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

7.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

7.2: 96 percent / tetrahydrofuran; H₂O / 4 h / 20 °C

8.1: aq. AcOH / tetrahydrofuran / 60 h / 20 °C

8.2: KOH / methanol / 20 h / 20 °C

9.1: 81 percent / toluene; tetrahydrofuran / 2 h / 120 °C

10.1: 94 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 2 h / 20 °C

11.1: Et₃N / diethyl ether / 2.5 h / -78 °C

12.1: diethyl ether / 17 h / -78 - -20 °C

12.2: aq. H₂O₂ / methanol; various solvent(s) / 2 h / 20 °C / pH 7

With barium dihydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; hydrogen; trityl tetrafluoroborate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; tert-butyl alcohol; 2.2: Horner-Wadsworth-Emmons chain extension / 3.1: Sharpless asymmetric dihydroxylation / 7.2: Horner-Wadsworth-Emmons chain extension / 8.1: intramolecular hetero-Michael addition;

DOI:10.1039/b504149j

Reference yield:

methyl (2E,4R)-4-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pent-2-enoate (194934-52-6) → (1S,4S,5R,6R)-10-chloro-4-hydroxy-1-(p-methoxybenzyloxy)-1-[4,5-(R,R)-bis(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-5-methyl-6-(triethylsiloxy)-decan-2-one (392692-62-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / aq. AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol / 16 h / 20 °C

2.1: 100 percent / NaHCO₃; H₂ / Pd(OH)2/C / methanol / 20 h / 20 °C

3.1: 97 percent / Ph₃CBF₄ / tetrahydrofuran / 0.5 h / 0 °C

4.1: 94 percent / DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

5.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

5.2: 96 percent / tetrahydrofuran; H₂O / 4 h / 20 °C

6.1: aq. AcOH / tetrahydrofuran / 60 h / 20 °C

6.2: KOH / methanol / 20 h / 20 °C

7.1: 81 percent / toluene; tetrahydrofuran / 2 h / 120 °C

8.1: 94 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 2 h / 20 °C

9.1: Et₃N / diethyl ether / 2.5 h / -78 °C

10.1: diethyl ether / 17 h / -78 - -20 °C

10.2: aq. H₂O₂ / methanol; various solvent(s) / 2 h / 20 °C / pH 7

With barium dihydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; methanesulfonamide; 4 A molecular sieve; AD-mix-β; hydrogen; trityl tetrafluoroborate; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation / 5.2: Horner-Wadsworth-Emmons chain extension / 6.1: intramolecular hetero-Michael addition;

DOI:10.1039/b504149j

upstream raw materials:

(2S,3R)-7-chloro-2-methyl-3-(triethylsiloxy)-heptanal

C₄₉H₆₇BO₈

(2R,4S,5R)-9-chloro-5-triethylsiloxy-2-hydroxy-4-methyl-nonan-3-one

(2R,4R,5R)-9-Chloro-4-methyl-5-triethylsilanyloxy-nonane-2,3-diol

Downstream raw materials:

(2R,4S,5R,6R)-6-(4-chlorobutyl)-2-methoxy-2-[[4,5-(R,R)-bis-(p-methoxybenzyloxy)-3-(R)-methyl-6-(R)-(2-methylallyl)-tetrahydropyran-2-(R)-yl]-((S)-p-methoxybenzyloxy)-methyl]-5-methyl-tetrahydropyran-4-ol

C₆₃H₉₆BClO₁₁Si

C₆₂H₉₄Cl₂O₁₂Si₂

C₆₃H₉₆Cl₂O₁₁Si₂

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