(E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.0^4,9]tetracos-14-ene-2,3,10,16-tetraone

Base Information

• Chemical Name: (E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.0^4,9]tetracos-14-ene-2,3,10,16-tetraone
• CAS No.: 131190-66-4
• Molecular Formula: C₃₈H₅₉NO₁₂
• Molecular Weight: 721.886

Synonyms:(E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.0^4,9]tetracos-14-ene-2,3,10,16-tetraone

Chemical Property of (E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.0^4,9]tetracos-14-ene-2,3,10,16-tetraone

Chemical Property:

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Technology Process of (E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.0^4,9]tetracos-14-ene-2,3,10,16-tetraone

There total 21 articles about (E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.0^4,9]tetracos-14-ene-2,3,10,16-tetraone 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: 2.5%

C53H93NO12Si2 (136358-59-3) → (E)-(8S,11R,17S,18S,19S,20S,22R)-1-Hydroxy-11-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-17-isopropyl-18,20-dimethoxy-12,12,22-trimethyl-10,16,24-trioxa-3-aza-tricyclo[17.4.1.03,8]tetracos-13-ene-2,9,15,23-tetraone + (E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.04,9]tetracos-14-ene-2,3,10,16-tetraone (131190-66-4)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 1h;

Reference yield:

<2R,S,3R,5S,6S,6(1S,2S)>-2-hydroxy-6-<2-(benzyloxy)-1-methoxy-3-methylbutyl>-5-methoxy-3-methyltetrahydropyran (136358-53-7,136358-54-8) → (E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.04,9]tetracos-14-ene-2,3,10,16-tetraone (131190-66-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 73.5 percent / acetonitrile / 72 h / Heating

2: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 - 20 °C

3: 60.4 percent / dihydroquinidine acetate, OsO₄ / toluene / 5 h

4: 96 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 2 h

5: 80 percent / 4A molecular sieves, camphorsulfonic acid / benzene; tetrahydrofuran / 2 h / Ambient temperature

6: 95 percent / dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.33 h

7: 90.8 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / -15 - -10 °C

8: N-metylmorpholine, (benzotriazolyl-1-oxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) / CH₂Cl₂ / 3 h / Ambient temperature

9: 10percent aq. HCl / tetrahydrofuran / 0.08 h

10: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

11: LiCl, diazobicycloundecene (DBU) / acetonitrile / 2.5 h

12: 67.5 percent / Et₂AlCl, propanedithiol / CH₂Cl₂ / 4 h / Ambient temperature

13: DMSO, trifluoroacetic anhydride / CH₂Cl₂ / 1 h

14: 5 mg / HF / acetonitrile / 1 h

With 4-methyl-morpholine; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; osmium(VIII) oxide; hydroquinidine acetate; 1,2-propanedithiol; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; hydrogen; diethylaluminium chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene;

Reference yield:

(2E,6S,7S,8R,9S)-7-hydroxy-6,8-dimethoxy-4,10-dimethyl-9-(phenylmethoxy)-2-undecenoic acid methyl ester (136358-37-7) → (E)-(1R,9S,12R,18S,19S,20S,21S,23R)-1-Hydroxy-12-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-18-isopropyl-19,21-dimethoxy-13,13,23-trimethyl-11,17,24-trioxa-4-aza-tricyclo[18.3.1.04,9]tetracos-14-ene-2,3,10,16-tetraone (131190-66-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 - 20 °C

2: 60.4 percent / dihydroquinidine acetate, OsO₄ / toluene / 5 h

3: 96 percent / H₂ / 10percent Pd(OH)2/C / ethyl acetate / 2 h

4: 80 percent / 4A molecular sieves, camphorsulfonic acid / benzene; tetrahydrofuran / 2 h / Ambient temperature

5: 95 percent / dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 0.33 h

6: 90.8 percent / aq. LiOH / tetrahydrofuran; methanol / 2 h / -15 - -10 °C

7: N-metylmorpholine, (benzotriazolyl-1-oxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) / CH₂Cl₂ / 3 h / Ambient temperature

8: 10percent aq. HCl / tetrahydrofuran / 0.08 h

9: Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

10: LiCl, diazobicycloundecene (DBU) / acetonitrile / 2.5 h

11: 67.5 percent / Et₂AlCl, propanedithiol / CH₂Cl₂ / 4 h / Ambient temperature

12: DMSO, trifluoroacetic anhydride / CH₂Cl₂ / 1 h

13: 5 mg / HF / acetonitrile / 1 h

With 4-methyl-morpholine; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; osmium(VIII) oxide; hydroquinidine acetate; 1,2-propanedithiol; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; hydrogen; diethylaluminium chloride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene;

upstream raw materials:

C₅₃H₉₃NO₁₂Si₂

2,2-dimethyl-3-(4-methoxyphenylmethoxy)propionaldehyde

(1R,2R,4R)-4-<(E)-2-bromo-1-propen-1-yl>-2-methoxy-1-<(triisopropylsilyl)oxy>cyclohexane

<2R,S,3R,5S,6S,6(1S,2S)>-2-hydroxy-6-<2-(benzyloxy)-1-methoxy-3-methylbutyl>-5-methoxy-3-methyltetrahydropyran

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