(2-alpha,3-alpha,5-alpha,22R,23R,24S)-2,3,22,23-tetrahydroxy-B-homo-7-oxaergostan-6-one

Base Information

• Chemical Name: (2-alpha,3-alpha,5-alpha,22R,23R,24S)-2,3,22,23-tetrahydroxy-B-homo-7-oxaergostan-6-one
• CAS No.: 72962-43-7
• Molecular Formula: C28H48O6
• Molecular Weight: 480.686
• Hs Code.: 29322090
• European Community (EC) Number: 688-467-2
• Wikipedia: Brassinolide,24-Epibrassinolide
• Mol file: 72962-43-7.mol

Synonyms:24-Epibrassinolide;C28H48O6;NSC325306;C28-H48-O6;72962-43-7;(2-alpha,3-alpha,5-alpha,22R,23R,24S)-2,3,22,23-tetrahydroxy-B-homo-7-oxaergostan-6-one

Chemical Property of (2-alpha,3-alpha,5-alpha,22R,23R,24S)-2,3,22,23-tetrahydroxy-B-homo-7-oxaergostan-6-one

Chemical Property:

• Appearance/Colour: Off-White Solid
• Vapor Pressure: 1.01E-18mmHg at 25°C
• Melting Point: 200-204 °C
• Refractive Index: 1.535
• Boiling Point: 633.716 °C at 760 mmHg
• PKA: 14.27±0.70(Predicted)
• Flash Point: 202.262 °C
• PSA: 107.22000
• Density: 1.142 g/cm³
• LogP: 3.39000
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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

Brassinolide>90% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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](C1CC[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: Brassinolide can be used as plant growth regulator. Plant growth regulator. Brassinolide has been used as a plant growth hormone.

Technology Process of (2-alpha,3-alpha,5-alpha,22R,23R,24S)-2,3,22,23-tetrahydroxy-B-homo-7-oxaergostan-6-one

There total 80 articles about (2-alpha,3-alpha,5-alpha,22R,23R,24S)-2,3,22,23-tetrahydroxy-B-homo-7-oxaergostan-6-one 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: 94.0%

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one (76987-58-1) → (3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one (72962-43-7)

Guidance literature:

With potassium hydroxide; In methanol; for 1h; Heating;

Reference yield: 74.0%

(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one (83066-72-2) → (3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one (72962-43-7) + (22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one (146205-07-4)

Guidance literature:

With trifluoroacetyl peroxide; In dichloromethane; at 22 ℃; for 1h;

DOI:10.1021/ja00541a045

Reference yield: 53.0%

(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol (91708-76-8) → (3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one (72962-43-7)

Guidance literature:

With trifluoroacetyl peroxide; trifluoroacetic acid; In chloroform; for 3h; Ambient temperature;

DOI:10.1021/jo961854y

upstream raw materials:

3-dehydroteasterone

castasterone

2,3,22,23-tetra-O-acetylcastasterone

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one

Refernces

• 1、 Sakakibara,Mori. "Improved synthesis of brassinolide". . p. 663 - 664. Retrieved 1983.
• 2、 Hurski,Ermolovich,Zhabinskii,Khripach. "The development and use of a general route to brassinolide, its biosynthetic precursors, metabolites and analogues". . p. 1446 - 1452. Retrieved 2015/01/30.
• 3、 Back, Thomas G.,Baron, Denise L.,Luo, Weide,Nakajima, Suanne K.. "Concise, improved procedure for the synthesis of brassinolide and some novel side-chain analogues". . p. 1179 - 1182. Retrieved 2007/10/03.