(2S)-N-[(4aS,6R,8S,8aR)-6-(2,3-dihydroxypropyl)-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide

Base Information

• Chemical Name: (2S)-N-[(4aS,6R,8S,8aR)-6-(2,3-dihydroxypropyl)-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide
• CAS No.: 115185-92-7
• Molecular Formula: C₂₄H₄₁NO₁₀
• Molecular Weight: 503.59
• Wikidata: Q105113873
• Mol file: 115185-92-7.mol

Synonyms:mycalamide A

Chemical Property of (2S)-N-[(4aS,6R,8S,8aR)-6-(2,3-dihydroxypropyl)-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 675.2°Cat760mmHg
• PKA: 12.32±0.20(Predicted)
• Flash Point: 362.2°C
• PSA: 145.17000
• Density: 1.25g/cm³
• LogP: 0.44910
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 503.27304650
• Heavy Atom Count: 35
• Complexity: 763

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

MYCALAMIDE A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(CC1=C)(C(C(=O)NC2C3C(C(C(C(O3)CC(CO)O)(C)C)OC)OCO2)O)OC)C
• Isomeric SMILES: C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)NC2[C@@H]3[C@@H]([C@H](C([C@H](O3)CC(CO)O)(C)C)OC)OCO2)O)OC)C

Technology Process of (2S)-N-[(4aS,6R,8S,8aR)-6-(2,3-dihydroxypropyl)-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide

There total 51 articles about (2S)-N-[(4aS,6R,8S,8aR)-6-(2,3-dihydroxypropyl)-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetamide 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: 90.0%

7-benzyloxy-O(17)-O(18)-carbonyl-mycalamide A → mycalamide A (115185-92-7)

Guidance literature:

With lithium hydroxide; In methanol; Ambient temperature;

DOI:10.3987/COM-95-S64

Reference yield: 78.0%

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester (855282-34-7) → mycalamide A (115185-92-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ja050728l

Reference yield: 69.0%

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester → mycalamide A (115185-92-7)

Guidance literature:

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-8-methoxy-7,7-dimethyl-6-((S)-2-oxo-[1,3]dioxolan-4-ylmethyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-phenylselanylmethyl-tetrahydro-pyran-2-yl)-methyl ester; With sodium periodate; In methanol; dichloromethane; water; for 2h;

With triethylamine; In toluene; at 110 ℃; for 0.166667h;

With lithium hydroxide; In methanol; water; for 2h;

DOI:10.1021/ol052943c

upstream raw materials:

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

(R)-1-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)ethane-1,2-diol

(R)-1-((2R,5R,6R)-2-Methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethanol

Acetic acid (S)-1-acetoxymethyl-2-((4aS,6R,8S,8aR)-4-amino-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-ethyl ester

Downstream raw materials:

Mycalamide A 18-mono-p-bromobenzoate

Mycalamide A 17,18-di-p-bromobenzoate

Mycalamide A 7,18-di-p-bromobenzoate

Mycalamide A tri-p-bromobenzoate