(E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

Base Information

Chemical Name:(E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal
CAS No.:256424-81-4
Molecular Formula:C₃₉H₅₄N₄O₁₀
Molecular Weight:738.879
Hs Code.:

(E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

Synonyms:(E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

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Chemical Property of (E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

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Technology Process of (E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

There total 3 articles about (E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal 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: 87.0%

: 256424-82-5
26(S),27(S)-dihydroxysanglifehrin A

: 256326-85-9
(2S,3R,4S,5S,6R,9S,11S)-9-ethyl-4-hydroxy-2-(((2S,3S)-6-hydroxy-3-methyltetrahydro-2H-pyran-2-yl)methyl)-3,5,11-trimethyl-1-oxa-7-azaspiro[5.5]undecan-8-one

: 256424-81-4
(E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 1h;
DOI:10.1021/jo9912395

Reference yield:

: 187148-13-6
(-)-sanglifehrin A

: 256424-81-4
(E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

Guidance literature:: Multi-step reaction with 2 steps

1: 70 percent / (DHQ)2PHAL; OsO₄; CH₃SO₂NH₂; K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

2: 87 percent / sodium periodate / tetrahydrofuran; H₂O / 1 h / 20 °C

With sodium periodate; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; water; tert-butyl alcohol; 1: Addition / 2: Decomposition;
DOI:10.1021/jo9912395

Reference yield:

: 870465-58-0
sanglifehrin A ketal

: 256424-81-4
(E)-3-[(13E,15E)-(3S,6S,9R,10R,11S,12S,18S,21S)-10,12-Dihydroxy-3-(3-hydroxy-benzyl)-6-isopropyl-11-methyl-2,5,8,20-tetraoxo-9-(3-oxo-butyl)-19-oxa-1,4,7,25-tetraaza-bicyclo[19.3.1]pentacosa-13,15-dien-18-yl]-but-2-enal

Guidance literature:: Multi-step reaction with 3 steps

1: 30 percent / TsOH; boric acid / tetrahydrofuran / 5 h / 20 °C

2: 70 percent / (DHQ)2PHAL; OsO₄; CH₃SO₂NH₂; K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

3: 87 percent / sodium periodate / tetrahydrofuran; H₂O / 1 h / 20 °C

With sodium periodate; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; boric acid; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; water; tert-butyl alcohol; 1: Ring cleavage / 2: Addition / 3: Decomposition;
DOI:10.1021/jo9912395