(22S,23S)-24-epibrassinolide

Base Information

• Chemical Name: (22S,23S)-24-epibrassinolide
• CAS No.: 78821-42-8
• Molecular Formula: C28H48 O6
• Molecular Weight: 480.686
• ChEMBL ID: CHEMBL1801925
• DSSTox Substance ID: DTXSID401045841
• Nikkaji Number: J399.546A
• Mol file: 78821-42-8.mol

Synonyms:78821-42-8;(22S,23S)-24-epibrassinolide;tris-Epibrassinolide;(22S,23S)-epibrassinolide;CHEMBL1801925;DTXSID401045841

Chemical Property of (22S,23S)-24-epibrassinolide

Chemical Property:

• PSA: 107.22000
• LogP: 3.39000
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 480.34508925
• Heavy Atom Count: 34
• Complexity: 755

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C)C(C(C(C)C1CCC2C1(CCC3C2COC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2COC(=O)[C@@H]4[C@@]3(C[C@H]([C@H](C4)O)O)C)C)[C@@H]([C@H]([C@H](C)C(C)C)O)O
• Uses: tris-Epibrassinolide can be used in biological study for epinasty in context of auxin input pathways and role of reactive oxygen species, nitric oxide and cytoskeleton structure in development of nastic phenotypes in A. thaliana.

Technology Process of (22S,23S)-24-epibrassinolide

There total 37 articles about (22S,23S)-24-epibrassinolide 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: 96.0%

(22R,23R)-22,23-dihydroxy-2α,3α-isopropylidenedioxy-B-homo-7-oxa-5α-campestan-6-one → (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-campestan-6-one (72962-43-7,78821-42-8,78821-43-9,80736-39-6,93860-61-8,93860-62-9,110453-84-4,113666-77-6,135559-12-5,140923-40-6)

Guidance literature:

With acetic acid; In water; at 60 ℃; for 1h;

DOI:10.1039/c4ob02197e

Reference yield:

(22E,24R)-B-Homo-7-oxa-5α-ergost-2,22-dien-6-one (124696-45-3) → 22,23,24-trisepibrassinolide (78821-42-8) + 24-epibrassinolide (78821-43-9)

Guidance literature:

With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In tetrahydrofuran; water; tert-butyl alcohol; for 48h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1055/s-1989-27273

Reference yield:

(R)-2-(1,3-dithian-2-yl)-3-methylbutan-1-ol (1418453-68-5) → (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-campestan-6-one (72962-43-7,78821-42-8,78821-43-9,80736-39-6,93860-61-8,93860-62-9,110453-84-4,113666-77-6,135559-12-5,140923-40-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine / diethyl ether / 0.25 h / 0 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - 20 °C / Inert atmosphere

3.2: 0.03 h / -78 °C / Inert atmosphere

4.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; ethanol / 0.08 h / 0 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 0.25 h / -78 °C / Inert atmosphere

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium chlorite; potassium bromide / aq. phosphate buffer; dichloromethane / 1.17 h / 0 °C / pH 7 / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / methanol / 0.17 h / 20 °C / Inert atmosphere

9.1: acetic acid / water / 1 h / 60 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; triethylamine; potassium bromide; In tetrahydrofuran; methanol; aq. phosphate buffer; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1039/c4ob02197e

upstream raw materials:

(R)-2-(1,3-dithian-2-yl)-3-methylbutan-1-ol

isovaleraldehyde

Refernces

• 1、 Seto, Hideharu,Fujioka, Shozo,Koshino, Hiroyuki,Yoshida, Shigeo,Watanabe, Tsuyoshi,Takatsuto, Suguru. "A general approach to synthesis of labeled brassinosteroids: Preparation of [25,26,27-2h7]brassinolide with 60% isotopic purity from the parent brassinolide". . p. 7525 - 7528. Retrieved 2007/10/03.
• 2、 Kametani, Tetsuji,Keino, Katsuyuki,Kigawa. Masaharu,Tsubuki, Masayoshi,Honda, Toshio. "STEREOCONTROLLED SYNTHESIS OF THE BRASSINOLIDE SIDE CHAIN VIA A PYRANONE DERIVATIVE". . p. 3141 - 3142. Retrieved 2007/10/02.