28-Norbrassinolide

Base Information

• Chemical Name: 28-Norbrassinolide
• CAS No.: 77736-43-7
• Molecular Formula: C₂₇H₄₆O₆
• Molecular Weight: 466.659
• DSSTox Substance ID: DTXSID00551143
• Nikkaji Number: J417.938B
• Wikidata: Q82430665
• Mol file: 77736-43-7.mol

Synonyms:28-Norbrassinolide;77736-43-7;28-Nor Brassinolide;(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R)-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one;DTXSID00551143;(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(3R,4R)-3,4-Dihydroxy-6-methylheptan-2-yl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Chemical Property of 28-Norbrassinolide

Chemical Property:

• PSA: 107.22000
• LogP: 2.93730
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 466.32943918
• Heavy Atom Count: 33
• Complexity: 725

Purity/Quality:

96% ^*data from raw suppliers

28-NorBrassinolide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(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](CC(C)C)O)O
• Uses: A metabolite of Brassinolide (B677050). A new type of modified brassinosteroids for enzyme-linked immunosorbent assay.

Technology Process of 28-Norbrassinolide

There total 19 articles about 28-Norbrassinolide 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: 88.0%

(22S,23S)-2α,3α,22,23-tetraacetoxy-B-homo-7-oxa-5α-cholestan-6-on (83456-52-4,83462-93-5) → (22S,23S)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-on (77736-43-7,78780-31-1,86695-23-0,86695-24-1)

Guidance literature:

With potassium hydroxide; In methanol; Heating;

Reference yield: 77.0%

(22R,23R)-2α,3α,22,23-tetrahydroxy-5α-cholestan-6-one (83464-85-1) → 28-norbrassinolide (77736-43-7)

Guidance literature:

With dihydrogen peroxide; trifluoroacetic anhydride; In dichloromethane; water; at -20 ℃; for 5h;

DOI:10.1080/00397910903318757

Reference yield: 58.0%

(22R,23R)-2α,3α,22,23-tetra-acetoxy-B-homo-7-oxa-5α-cholestan-6-one (83462-93-5) → 28-norbrassinolide (77736-43-7)

Guidance literature:

(22R,23R)-2α,3α,22,23-tetra-acetoxy-B-homo-7-oxa-5α-cholestan-6-one; With potassium hydroxide; In methanol; for 6h; Reflux;

With hydrogenchloride; In water; at 20 ℃; for 2h; pH=2;

DOI:10.1016/j.steroids.2014.08.020

upstream raw materials:

Acetic acid (3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8-acetoxy-1-((1S,2R,3R)-2,3-diacetoxy-1,5-dimethyl-hexyl)-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-9-yl ester

C₂₅H₄₀O₅

C₂₅H₃₈O₅

C₂₈H₄₄O₇