2-[(14Z)-9-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde

Base Information

• Chemical Name: 2-[(14Z)-9-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde
• CAS No.: 35834-26-5
• Molecular Formula: C31H51 N O9
• Molecular Weight: 581.747
• European Community (EC) Number: 252-742-1
• ChEMBL ID: CHEMBL2357105
• Wikidata: Q104397051
• Wikipedia: Rosaramicin
• Mol file: 35834-26-5.mol

Synonyms:DTXCID2026361;2-[(14Z)-9-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde;2-[(7R,8S,9S,10R,12R,14E,16S)-9-[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde;CAS-35834-26-5;DTXSID4046361;NCGC00163616-01;NCGC00183657-01;35834-26-5;SCHEMBL134724;CHEMBL2357105;Tox21_112063;Tox21_113415;NS00011676

Chemical Property of 2-[(14Z)-9-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde

Chemical Property:

• Melting Point: 119-122°
• Refractive Index: 1.6310 (estimate)
• Boiling Point: 734.7°Cat760mmHg
• Flash Point: 398.1°C
• PSA: 135.13000
• Density: 1.17g/cm³
• LogP: 2.67040
• Storage Temp.: 2-8°C
• Solubility.: methanol: 10 mg/mL, clear, light yellow
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 581.35638220
• Heavy Atom Count: 41
• Complexity: 941

Purity/Quality:

98%,99%, ^*data from raw suppliers

Rosamicin from Micromonospora rosaria, ~98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(C2C(O2)(C=CC(=O)C(CC(C(C(C(CC(=O)O1)O)C)OC3C(C(CC(O3)C)N(C)C)O)CC=O)C)C)C
• Isomeric SMILES: CCC1C(C2[C@@](O2)(/C=C/C(=O)[C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)O)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)CC=O)C)C)C
• Uses: Antibacterial.

Technology Process of 2-[(14Z)-9-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde

There total 27 articles about 2-[(14Z)-9-[4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-3-ethyl-7-hydroxy-2,8,12,16-tetramethyl-5,13-dioxo-4,17-dioxabicyclo[14.1.0]heptadec-14-en-10-yl]acetaldehyde 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: 43.0%

12,13-de-epoxy-12,13-didehydrorosaramicin (56689-42-0) → rosaramicin (35834-26-5)

Guidance literature:

With JuvD-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) → rosaramicin (35834-26-5)

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: JuvD-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 → rosaramicin (35834-26-5)

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: JuvD-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:

rosaramicin N-oxide

12,13-de-epoxy-12,13-didehydrorosamicin 20-dimethyl acetal

rosaramicin 20-dimethyl acetal 3'-N-oxide

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

Downstream raw materials:

12,13-de-epoxy-12,13-didehydrorosamicin 20-dimethyl acetal

12,13-de-epoxy-12,13-didehydrorosaramicin

20-deoxorosaramicin-20-diphenylthioacetal

11(R)-20-deoxo-10,11-dihydro-11-phenylthiorosaramicin 20-diphenylthioacetal

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