Tylonolide, 5-O-(3,4,6-trideoxy-3-(dimethylamino)-beta-D-glucopyranosyl)-

Base Information

• Chemical Name: Tylonolide, 5-O-(3,4,6-trideoxy-3-(dimethylamino)-beta-D-glucopyranosyl)-
• CAS No.: 80240-61-5
• Molecular Formula: C₃₁H₅₁NO₉
• Molecular Weight: 581.747
• Mol file: 80240-61-5.mol

Synonyms:4'-deoxymycaminosyl tylonolide;4'-deoxymycaminosyltylonolide;5-O-(4-deoxymycaminosyl)tylonolide

Chemical Property of Tylonolide, 5-O-(3,4,6-trideoxy-3-(dimethylamino)-beta-D-glucopyranosyl)-

Chemical Property:

• Vapor Pressure: 5.69E-27mmHg at 25°C
• Boiling Point: 764.3°Cat760mmHg
• PKA: 13.49±0.70(Predicted)
• Flash Point: 416.1°C
• Density: 1.16g/cm³
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 581.35638220
• Heavy Atom Count: 41
• Complexity: 919

Purity/Quality:

99% ^*data from raw suppliers

4'-DEOXYMYCAMINOSYLTYLONOLIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC1C(C=C(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC2C(C(CC(O2)C)N(C)C)O)CC=O)C)C)CO
• Isomeric SMILES: CC[C@@H]1[C@H](/C=C(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]2[C@@H]([C@H](C[C@H](O2)C)N(C)C)O)CC=O)C)\C)CO

Technology Process of Tylonolide, 5-O-(3,4,6-trideoxy-3-(dimethylamino)-beta-D-glucopyranosyl)-

There total 24 articles about Tylonolide, 5-O-(3,4,6-trideoxy-3-(dimethylamino)-beta-D-glucopyranosyl)- 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: 47.0%

12,13-de-epoxy-12,13-didehydrorosaramicin (56689-42-0) → 5-O-desosaminyltylonolide (80240-61-5)

Guidance literature:

With MycCI-RhFRED; In water; at 30 ℃; Enzymatic reaction;

DOI:10.1021/jacs.7b02875

Reference yield:

(S)-4-benzyl-3-((4S,5R,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylhept-2-enoyl)oxazolidin-2-one (1403991-96-7) → 5-O-desosaminyltylonolide (80240-61-5)

Guidance literature:

Multi-step reaction with 10 steps

1: lithium borohydride; methanol / tetrahydrofuran / 1.5 h / 0 - 20 °C

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

3: caesium carbonate / isopropyl alcohol / 24 h / 0 - 20 °C

4: Divinyl sulfone; tributylphosphine / dichloromethane / 0.5 h / 0 °C

5: hydrogen fluoride / acetonitrile; water / 35 h / -20 °C / Darkness

6: nicotinamide adenine dinucleotide phosphate; glucose-6-phosphate; glucose-6-phosphate dehydrogenase / aq. phosphate buffer; water / 2.3 h / 30 °C / pH 7.2 / Enzymatic reaction

7: acetyl-narbonolide / water; dimethyl sulfoxide / 24 h / 28 °C / Enzymatic reaction

8: Tyll-RhFRED / water / 30 °C / Enzymatic reaction

9: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; [2,2]bipyridinyl; 1-methyl-1H-imidazole / acetonitrile / 1.5 h / 20 °C

10: MycCI-RhFRED / water / 30 °C / Enzymatic reaction

With 1-methyl-1H-imidazole; Divinyl sulfone; methanol; [2,2]bipyridinyl; lithium borohydride; glucose-6-phosphate dehydrogenase; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; glucose-6-phosphate; tributylphosphine; nicotinamide adenine dinucleotide phosphate; hydrogen fluoride; copper(I) triflate; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; acetonitrile; 3: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/jacs.7b02875

Reference yield:

(E,4S,5R)-5-tert-butyldimethylsilyloxy-2,4-dimethylhept-2-ene-1-ol → 5-O-desosaminyltylonolide (80240-61-5)

Guidance literature:

Multi-step reaction with 9 steps

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C

2: caesium carbonate / isopropyl alcohol / 24 h / 0 - 20 °C

3: Divinyl sulfone; tributylphosphine / dichloromethane / 0.5 h / 0 °C

4: hydrogen fluoride / acetonitrile; water / 35 h / -20 °C / Darkness

5: nicotinamide adenine dinucleotide phosphate; glucose-6-phosphate; glucose-6-phosphate dehydrogenase / aq. phosphate buffer; water / 2.3 h / 30 °C / pH 7.2 / Enzymatic reaction

6: acetyl-narbonolide / water; dimethyl sulfoxide / 24 h / 28 °C / Enzymatic reaction

7: Tyll-RhFRED / water / 30 °C / Enzymatic reaction

8: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) triflate; [2,2]bipyridinyl; 1-methyl-1H-imidazole / acetonitrile / 1.5 h / 20 °C

9: MycCI-RhFRED / water / 30 °C / Enzymatic reaction

With 1-methyl-1H-imidazole; Divinyl sulfone; [2,2]bipyridinyl; glucose-6-phosphate dehydrogenase; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; glucose-6-phosphate; tributylphosphine; nicotinamide adenine dinucleotide phosphate; hydrogen fluoride; copper(I) triflate; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; In aq. phosphate buffer; dichloromethane; water; dimethyl sulfoxide; isopropyl alcohol; acetonitrile; 2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1021/jacs.7b02875

upstream raw materials:

(S)-4-benzyl-3-((4S,5R,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylhept-2-enoyl)oxazolidin-2-one

(4S,5R,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethylhept-2-enal

(+)-(4S)-3-<(2'R)-2'-((benzyloxy)methyl)butanoyl>-4-benzyl-2-oxazolidinone

(S)-2-((benzyloxy)methyl)butan-1-ol

Refernces