Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester
• CAS No.: 113161-48-1
• Molecular Formula: C₃₈H₄₈O₉
• Molecular Weight: 648.794
• Mol file: 113161-48-1.mol

Synonyms:Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester

There total 35 articles about Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester 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: 56.0%

(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol (113161-47-0) + 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose (3068-31-3) → Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester (113161-48-1)

Guidance literature:

(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol; With sodium hydride; In acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose; In acetonitrile; for 1.5h; Inert atmosphere;

DOI:10.1021/jacs.6b02624

Reference yield:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide (3068-31-3) + (4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol (113161-47-0) → Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester (113161-48-1)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at 20 ℃;

DOI:10.1021/jo00242a053

Reference yield:

(1S,2S,5S)-5-(1-hydroxypropan-2-yl)-2-methylcyclohexanol → Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-[(4R,6S,6aR,9S)-2-benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3-yl ester (113161-48-1)

Guidance literature:

Multi-step reaction with 29 steps

1: pyridine

2: pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂

3: aq. KOH

4: pyridinium chlorochromate (PCC) , NaOAc / CH₂Cl₂

5: NaClO₂, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

6: aq. acetic acid / 80 °C

7: 67 percent / p-toluenesulfonic acid / toluene / Heating

8: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

9: H₂O₂

10: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

11: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

12: Et₃N, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂

13: lithium triethylborohydride / tetrahydrofuran

14: pyridinium chlorochromate (PCC) / CH₂Cl₂

15: NaH / dioxane

16: Et₃N / hexane

17: 1.) TiCl₄, 2.) NaOMe / 1.) CH₂Cl₂, -78 deg C, 4 h, 2.) MeOH, 24 h

18: m-chloroperbenzoic acid (MCPBA), NaHCO₃ / CHCl₃ / 55 °C

19: SnCl₄ / CH₂Cl₂ / 20 °C

20: K₂CO₃ / dimethylsulfoxide

21: imidazole / dimethylformamide / 45 °C

22: diisopropylaluminum hydride (DIBAL) / CH₂Cl₂ / 20 °C

23: pyridinium chlorochromate (PCC) / CH₂Cl₂

24: m-chloroperbenzoic acid (MCPBA), Na₂HPO₄ / CHCl₃ / 3 h / 20 °C

25: tetrabutylammonium fluoride (TBAF), acetic acid / tetrahydrofuran

26: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂, -40 deg C

27: tetrahydrofuran / 0.5 h / 20 °C

28: (dimethylamino)formaldehyde dineopentyl acetal, 4,4-methylenebis(2,6-di-tert-butylphenol) / CHCl₃ / 72 h / 55 °C

29: AgOTf, tetramethylurea / CH₂Cl₂ / 20 °C

With pyridine; 1H-imidazole; dmap; potassium hydroxide; sodium chlorite; disodium hydrogenphosphate; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; 2-methyl-but-2-ene; oxalyl dichloride; diisopropyl aluminum hydride; dimethylsulfide; 4,4'-Methylenebis(2,6-di-tert-butylphenol); tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium methylate; sodium acetate; silver trifluoromethanesulfonate; pyridinium p-toluenesulfonate; titanium tetrachloride; tin(IV) chloride; sodium hydride; lithium triethylborohydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; N,N-dimethylformamide dineopentyl acetal; tetramethylurea; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo00242a053

upstream raw materials:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide

(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

(2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone

(1S,5S,8S)-8-Methyl-4-methylene-2-oxa-bicyclo[3.3.1]nonan-3-one

Downstream raw materials:

(2S,3R,4S,5R)-2-[(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3,4,5-triol