(10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester

Base Information

• Chemical Name: (10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester
• CAS No.: 133523-45-2
• Molecular Formula: C₃₇H₆₆O₁₀
• Molecular Weight: 670.925

Synonyms:(10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester

Chemical Property of (10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester

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Technology Process of (10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester

There total 6 articles about (10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl 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: 45.0%

methanol (67-56-1) + Tacrolimus (104987-11-3) → (S)-2-Benzyl-hexahydro-pyrido[1,2-a]pyrazine-1,4-dione (133523-43-0) + (10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester (133523-45-2) + (10E,18E)-(2R,4S,5R,6S,8S,12R,15S,16R,17S)-12-Allyl-5,15,17-trihydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-13-oxo-nonadeca-10,18-dienoic acid methyl ester (133523-44-1) + (E)-(2R,4S,5R,6S,8S,12R)-12-{(4S,5R,6S)-2,4-Dihydroxy-6-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-5-methyl-tetrahydro-pyran-2-yl}-5-hydroxy-4,6-dimethoxy-2,8,10-trimethyl-pentadeca-10,14-dienoic acid methyl ester (133548-78-4)

Guidance literature:

With sodium cyanoborohydride; benzylamine; at 23 ℃; for 14h;

DOI:10.1021/jo00008a055

Reference yield: 40.0%

methanol (67-56-1) + 22(S)-dihydro-FK-506 (118949-52-3,124152-71-2,137694-88-3) → (10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester (133523-45-2)

Guidance literature:

With sodium cyanoborohydride; benzylamine; at 23 ℃; for 24h;

DOI:10.1021/jo00008a055

Reference yield: 35.0%

Tacrolimus (104987-11-3) + benzylamine (100-46-9) → (S)-2-Benzyl-hexahydro-pyrido[1,2-a]pyrazine-1,4-dione (133523-43-0) + (10E,18E)-(2R,4S,5R,6S,8S,12R,13S,15S,16R,17S)-12-Allyl-5,13,15,17-tetrahydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-nonadeca-10,18-dienoic acid methyl ester (133523-45-2) + (10E,18E)-(2R,4S,5R,6S,8S,12R,15S,16R,17S)-12-Allyl-5,15,17-trihydroxy-19-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-4,6-dimethoxy-2,8,10,16,18-pentamethyl-13-oxo-nonadeca-10,18-dienoic acid methyl ester (133523-44-1) + (E)-(2R,4S,5R,6S,8S,12R)-12-{(4S,5R,6S)-2,4-Dihydroxy-6-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-5-methyl-tetrahydro-pyran-2-yl}-5-hydroxy-4,6-dimethoxy-2,8,10-trimethyl-pentadeca-10,14-dienoic acid methyl ester (133548-78-4)

Guidance literature:

With sodium cyanoborohydride; In methanol; at 23 ℃; for 14h;

DOI:10.1021/jo00008a055

upstream raw materials:

methanol

Tacrolimus

22(S)-dihydro-FK-506

benzylamine

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