(3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone

Base Information

• Chemical Name: (3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone
• CAS No.: 135635-56-2
• Molecular Formula: C₄₄H₆₉NO₁₂
• Molecular Weight: 804.031
• Mol file: 135635-56-2.mol

Synonyms:

Chemical Property of (3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone

There total 3 articles about (3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone 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: 15.0%

Tacrolimus (104987-11-3) → (S)-1-[2-[(2R,3R,5S,6R)-6-[(1S,3S,5E,7R,9E,11R,12S,13E)-7-(2-propen-1-yl)-12-hydroxy-14-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methoxy-3,5,11,13-tetramethyl-8-oxotetradeca-5,9,13-trien-1-yl]-2-hydroxy-5-methoxy-3-methyltetrahydro-2H-pyran-2-yl]-2-oxoacetyl]piperidine-2-carboxylic acid + (3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone (104987-11-3,129212-35-7,135635-56-2,144490-63-1)

Guidance literature:

With DBN; In dichloromethane; at 0 ℃;

DOI:10.1016/j.ejps.2012.12.001

Reference yield: 14.7%

Tacrolimus (104987-11-3) → (3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone (104987-11-3,129212-35-7,135635-56-2,144490-63-1)

Guidance literature:

With 1,5-diazabicyclo[4.3.0]-non-2-ene; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/np9007975

Reference yield: 10.0%

Tacrolimus (104987-11-3) → (3S,4R,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-14,16-dimethoxy-15,19-epoxy-19-hydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-8,11,12,13,14,15,16,17,18,19,24,25,26,26a-tetradecahydro-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone + (3S,4R,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-14,16-dimethoxy-15,19-epoxy-19-hydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-8,11,12,13,14,15,16,17,18,19,24,25,26,26a-tetradecahydro-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone (104987-16-8) + (3S,4R,5S,8S,9E,12S,14S,15R,16S,18R,19R,26aS)-5,19-dihydroxy-14,16-dimethoxy-15,19-epoxy-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-8-(2-propen-1-yl)-4,10,12,18-tetramethyl-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone (104987-11-3,129212-35-7,135635-56-2,144490-63-1)

Guidance literature:

With iodine; In toluene; for 6.5h; Reflux;

DOI:10.1016/j.ejps.2012.12.001

upstream raw materials:

Tacrolimus

Downstream raw materials:

(13E,20E)-(1R,9S,12R,15S,16S,19S,23S,25S,26R,27S,29R)-19-Allyl-1,16-dihydroxy-12-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-25,27-dimethoxy-13,15,21,23,29-pentamethyl-11,30-dioxa-4-aza-tricyclo[24.3.1.0^4,9]triaconta-13,20-diene-2,3,10,18-tetraone

(13E,16E,20E)-(1R,9S,12R,15R,19S,23S,25S,26R,27S,29R)-19-Allyl-1-hydroxy-12-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-25,27-dimethoxy-13,15,21,23,29-pentamethyl-11,30-dioxa-4-aza-tricyclo[24.3.1.0^4,9]triaconta-13,16,20-triene-2,3,10,18-tetraone