Hemanthidine

Base Information

• Chemical Name: Hemanthidine
• CAS No.: 466-73-9
• Deprecated CAS: 21480-48-8,11002-52-1
• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.342
• UNII: 6DB9318OGJ
• Nikkaji Number: J117.053H
• Wikidata: Q27896532
• ChEMBL ID: CHEMBL465820
• Mol file: 466-73-9.mol

Synonyms:haemanthidine;hemanthidine

Chemical Property of Hemanthidine

Chemical Property:

• Vapor Pressure: 1.58E-11mmHg at 25°C
• Boiling Point: 517.3°C at 760 mmHg
• Flash Point: 266.7°C
• Density: 1.51g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 317.12632271
• Heavy Atom Count: 23
• Complexity: 527

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1CC2C3(C=C1)C(CN2C(C4=CC5=C(C=C34)OCO5)O)O
• Isomeric SMILES: CO[C@H]1C[C@H]2[C@@]3(C=C1)[C@H](CN2[C@H](C4=CC5=C(C=C34)OCO5)O)O

Technology Process of Hemanthidine

There total 27 articles about Hemanthidine 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:

2ξ-hydroxy-3c-methoxy-6-oxo-(4ar)-2,3,4,4a,5,6-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridine-11bt-carboxylic acid → rac-(11S)-3α-methoxy-crin-1-ene-6β,11-diol (466-73-9,545-66-4,28405-98-3,33172-28-0,60944-31-2)

Guidance literature:

Multi-step reaction with 6 steps

1: dimethylformamide

2: Py

3: (i) KOH, THF, (ii) SOCl₂

4: K₂CO₃ / dioxane

5: HCl / CH₂Cl₂

6: (i) disiamylborane, (ii) Ac₂O, BF₃-Et₂O, (iii) DABCO, (iv) LiAH₄, THF

With pyridine; hydrogenchloride; potassium carbonate; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00832a027

Reference yield:

2ξ-methanesulfonyloxy-3c-methoxy-6-oxo-(4ar)-2,3,4,4a,5,6-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridine-11bt-carbonyl chloride (54022-44-5) → rac-(11S)-3α-methoxy-crin-1-ene-6β,11-diol (466-73-9,545-66-4,28405-98-3,33172-28-0,60944-31-2)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / dioxane

2: HCl / CH₂Cl₂

3: (i) disiamylborane, (ii) Ac₂O, BF₃-Et₂O, (iii) DABCO, (iv) LiAH₄, THF

With hydrogenchloride; potassium carbonate; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja00832a027

Reference yield:

2ξ-hydroxy-3c-methoxy-6-oxo-(4ar)-2,3,4,4a,5,6-hexahydro-1H-[1,3]dioxolo[4,5-j]phenanthridine-11bt-carboxylic acid 2-oxo-2-phenyl-ethyl ester (28406-01-1) → d,l-Haemanthidin (466-73-9,545-66-4,28405-98-3,33172-28-0,60944-31-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / (mesylation)

2: (i) (saponification), (ii) SOCl₂, (iii) /BRN= 102415/

3: HCl

4: (i) disiamylborane, THF, (ii) (acetylation), (iii) DABCO, (iv) LiAlH₄

With hydrogenchloride; In pyridine;

DOI:10.1021/ja00721a053

upstream raw materials:

rac-(11S)-3α,6ξ-dimethoxy-crin-1-en-11-ol

rac-2ξ-methanesulfonyloxy-3α-methoxy-crinane-6,11-dione

3a-benzo[1,3]dioxol-5-yl-6c-methoxy-(3ar,7ac)-octahydro-indole-3t,5t-diol

rac-(11S)-2β,11-diacetoxy-3α,6ξ-dimethoxy-crinane

Downstream raw materials:

pretazettine

tazettine

N-Demethyl-6a-epi-3-epi-macronin

pretazettine