6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one

Base Information

Chemical Name:6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one
CAS No.:631900-19-1
Molecular Formula:C₂₇H₃₆O₇Si
Molecular Weight:500.664
Hs Code.:

Synonyms:6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one

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Chemical Property of 6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one

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Technology Process of 6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one

There total 17 articles about 6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one 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: 69.0%

: 631900-11-3
2-{(1S,2R,4S,6S)-6-(tert-butyldimethylsilyloxy)-2,4-(dimethyl)methylendioxy-1-(2-methoxyethoxymethoxy)-2-[(4-methoxy-6-oxopyran-2-yl)methyl]cyclohexyl}-1-phenylethanone

: 631900-19-1
6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one

Guidance literature:: With acetic acid; trifluoroacetic acid; In tetrahydrofuran; water; at 20 ℃; for 1.5h;
DOI:10.1002/anie.200351455

Reference yield:

: 675-10-5
4-hydroxy-6-methyl-2-pyron

: 631900-19-1
6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: t-BuLi / tetrahydrofuran; pentane / -78 - 0 °C

1.2: 64 percent / tetrahydrofuran; pentane / 48 h / -78 °C

2.1: 92 percent / K₂CO₃ / acetone / 12 h / 20 °C

3.1: 94 percent / HF*pyridine; pyridine / tetrahydrofuran / 12 h / 20 °C

4.1: 96 percent / 2-iodoxybenzoic acid / dimethylsulfoxide / 4 h / 20 °C

5.1: L-selectride / tetrahydrofuran / 2 h / -78 °C

5.2: 97 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0.5 h / 0 °C

6.1: 90 percent / PPTS / 1,2-dichloro-ethane / 0 - 20 °C

7.1: 85 percent / aq. NaIO₄; AcONa; OsO₄ / tetrahydrofuran / 3 h / 20 °C

8.1: 89 percent / tetrahydrofuran; diethyl ether / 1 h / -78 °C

9.1: 91 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 3 h / 20 °C

10.1: 69 percent / aq. AcOH; CF₃COOH / tetrahydrofuran / 1 h / 20 °C

With pyridine; sodium periodate; osmium(VIII) oxide; tert.-butyl lithium; sodium acetate; pyridinium p-toluenesulfonate; L-Selectride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone; pentane; 8.1: Grignard addition;
DOI:10.1002/chem.200500640

Reference yield:

: 631900-28-2
4-methoxy-6-([(1S,2S,3S)-2-allyl-3-(tert-butyldimethylsilyloxy)-1-hydroxy-2-(2-methoxyethoxymethoxy)-5-oxocyclohexyl]methyl)-2H-pyran-2-one

: 631900-19-1
6-{(1R,3S,4S,6S,8R)-[4-(tert-butyldimethylsilyloxy)-3-hydroxy-1-phenyl-9,10-dioxatricyclo[4.3.1.0][3.8]dec-8-yl]methyl}-4-methoxy-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: L-selectride / tetrahydrofuran / 2 h / -78 °C

1.2: 97 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 0.5 h / 0 °C

2.1: 90 percent / PPTS / 1,2-dichloro-ethane / 0 - 20 °C

3.1: 85 percent / aq. NaIO₄; AcONa; OsO₄ / tetrahydrofuran / 3 h / 20 °C

4.1: 89 percent / tetrahydrofuran; diethyl ether / 1 h / -78 °C

5.1: 91 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 3 h / 20 °C

6.1: 69 percent / aq. AcOH; CF₃COOH / tetrahydrofuran / 1 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium acetate; pyridinium p-toluenesulfonate; L-Selectride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; 4.1: Grignard addition;
DOI:10.1002/chem.200500640