Bacteriohopanetetrol

Base Information

• Chemical Name: Bacteriohopanetetrol
• CAS No.: 51024-98-7
• Molecular Formula: C₃₅H₆₂O₄
• Molecular Weight: 546.875
• ChEMBL ID: CHEMBL442840
• DSSTox Substance ID: DTXSID401046368
• Metabolomics Workbench ID: 29151,134098,163801
• Nikkaji Number: J1.991.161F
• Mol file: 51024-98-7.mol

Synonyms:32,33,34,35-bacteriohopanetetrol;32,33,34,35-BHTT;bacteriohopane-32,33,34,35-tetrol;bacteriohopane-tetrol;bacteriohopanetetrol;tetrahydroxybacteriohopane

Chemical Property of Bacteriohopanetetrol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 646.755°C at 760 mmHg
• Flash Point: 252.961°C
• Density: 1.052g/cm³
• XLogP3: 9.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 546.46481045
• Heavy Atom Count: 39
• Complexity: 888

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CCC(C(C(CO)O)O)O)C1CCC2(C1CCC3(C2CCC4C3(CCC5C4(CCCC5(C)C)C)C)C)C
• Isomeric SMILES: C[C@H](CC[C@H]([C@H]([C@H](CO)O)O)O)[C@H]1CC[C@]2([C@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCCC5(C)C)C)C)C)C

Technology Process of Bacteriohopanetetrol

There total 52 articles about Bacteriohopanetetrol 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:

(1S,2S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-((3R,5aR,5bR,11aS,13bS)-5a,5b,8,8,11a,13b-hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-hexane-1,2-diol (112275-87-3) → (2R,3S,4S)-7-((3R,5aR,5bR,11aS,13bS)-5a,5b,8,8,11a,13b-Hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-octane-1,2,3,4-tetraol (51024-98-7,144179-03-3,144179-11-3)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; methanol; at 20 ℃; for 12h;

DOI:10.1021/jo00273a034

Reference yield:

2-(30'-hopyl)ethanol (62139-14-4) → (2R,3S,4S)-7-((3R,5aR,5bR,11aS,13bS)-5a,5b,8,8,11a,13b-Hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-octane-1,2,3,4-tetraol (51024-98-7,144179-03-3,144179-11-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / methyltriphenoxyphosphonium iodide / tetrahydrofuran; dimethylformamide; hexamethylphosphoric acid triamide / 0.25 h / 20 °C

2: 100 percent / 0.33 h / 140 °C

3: n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 0.08 h / 20 °C

4: 20 °C

5: 2.5 mg / N-methylmorpholine N-oxide (NMO), osmium tetraoxide / tetrahydrofuran; acetone; H₂O; 2-methyl-propan-2-ol / 12 h / 20 °C

6: 10percent aq. H₂SO₄ / tetrahydrofuran; methanol / 12 h / 20 °C

With osmium(VIII) oxide; n-butyllithium; sulfuric acid; methyltriphenoxyphosphonium iodide; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/jo00273a034

Reference yield:

2-(30'-hopyl)ethyl iodide (120446-12-0) → (2R,3S,4S)-7-((3R,5aR,5bR,11aS,13bS)-5a,5b,8,8,11a,13b-Hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-octane-1,2,3,4-tetraol (51024-98-7,144179-03-3,144179-11-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / 0.33 h / 140 °C

2: n-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 0.08 h / 20 °C

3: 20 °C

4: 2.5 mg / N-methylmorpholine N-oxide (NMO), osmium tetraoxide / tetrahydrofuran; acetone; H₂O; 2-methyl-propan-2-ol / 12 h / 20 °C

5: 10percent aq. H₂SO₄ / tetrahydrofuran; methanol / 12 h / 20 °C

With osmium(VIII) oxide; n-butyllithium; sulfuric acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo00273a034

upstream raw materials:

(1S,2S)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-5-((3R,5aR,5bR,11aS,13bS)-5a,5b,8,8,11a,13b-hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-hexane-1,2-diol

2-(30'-hopyl)ethanol

2-(30'-hopyl)ethyl iodide

<2-(30'-hopyl)ethyl>triphenylphosphonium iodide

Downstream raw materials:

Acetic acid (R)-4-((3R,5aR,5bR,11aS,13bS)-hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-1-((1R,2S)-1,2,3-triacetoxy-propyl)-pentyl ester

Acetic acid (R)-4-((3R,5aR,5bR,11aS,13bS)-hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-1-((1R,2R)-1,2,3-triacetoxy-propyl)-pentyl ester

Acetic acid (R)-4-((3R,5aR,5bR,11aS,13bS)-hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-1-((1S,2S)-1,2,3-triacetoxy-propyl)-pentyl ester

Acetic acid (R)-4-((3R,5aR,5bR,11aS,13bS)-hexamethyl-icosahydro-cyclopenta[a]chrysen-3-yl)-1-((1S,2R)-1,2,3-triacetoxy-propyl)-pentyl ester