Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

Base Information

Chemical Name:Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester
CAS No.:850752-99-7
Molecular Formula:C₃₆H₄₄O₁₁
Molecular Weight:652.739
Hs Code.:

Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

Synonyms:Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

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Chemical Property of Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

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Technology Process of Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

There total 15 articles about Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-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: 91.0%

: 850753-12-7
Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aS,12R,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-7a-methoxy-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

: 850752-99-7
Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

Guidance literature:: With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃;
DOI:10.1016/j.tetlet.2005.02.039

Reference yield:

: 149342-25-6,92131-91-4
((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate

: 850752-99-7
Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: K₂CO₃ / methanol

1.2: 90 percent / NaH / tetrahydrofuran; dimethylformamide

2.1: 83 percent / DBU / RhCl(PPh₃)3 / ethanol / 60 °C

3.1: OsO₄; NMO / acetone

3.2: 93 percent / DMAP / pyridine

4.1: 90 percent / SnCl₄ / CH₂Cl₂ / -20 - 0 °C

5.1: K₂CO₃ / methanol

5.2: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: 88 percent / m-CPBA / CH₂Cl₂ / -40 - 0 °C

7.1: SmI₂ / tetrahydrofuran / -100 °C

7.2: 72 percent / DMAP / pyridine

8.1: CSA / CH₂Cl₂

8.2: 52 percent / DMAP / pyridine

9.1: 91 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / -20 °C

With triethylsilane; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; tin(IV) chloride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; 5.2: Swern oxidation;
DOI:10.1016/j.tetlet.2005.02.039

Reference yield:

: 2873-29-2
D-glucal triacetate

: 850752-99-7
Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aR,12S,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 78 percent / Et₃SiH; BF₃*Et₂O / acetonitrile / -20 °C

2.1: K₂CO₃ / methanol

2.2: 90 percent / NaH / tetrahydrofuran; dimethylformamide

3.1: 83 percent / DBU / RhCl(PPh₃)3 / ethanol / 60 °C

4.1: OsO₄; NMO / acetone

4.2: 93 percent / DMAP / pyridine

5.1: 90 percent / SnCl₄ / CH₂Cl₂ / -20 - 0 °C

6.1: K₂CO₃ / methanol

6.2: 92 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

7.1: 88 percent / m-CPBA / CH₂Cl₂ / -40 - 0 °C

8.1: SmI₂ / tetrahydrofuran / -100 °C

8.2: 72 percent / DMAP / pyridine

9.1: CSA / CH₂Cl₂

9.2: 52 percent / DMAP / pyridine

10.1: 91 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / -20 °C

With triethylsilane; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tin(IV) chloride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; RhCl(PPh₃)3; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; acetonitrile; 6.2: Swern oxidation;
DOI:10.1016/j.tetlet.2005.02.039