6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

Base Information

Chemical Name:6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one
CAS No.:631900-31-7
Molecular Formula:C₃₄H₅₂O₁₀Si
Molecular Weight:648.866
Hs Code.:

6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

Synonyms:6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

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Chemical Property of 6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

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Technology Process of 6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

There total 15 articles about 6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-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: 89.0%

: phenylmagnesium bromide

: 631900-18-0
2-{(1S,2R,4S,6S)-6-(tert-butyldimethylsilyloxy)-2,4-(dimethyl)methylendioxy-1-(2-methoxyethoxymethoxy)-2-[(4-methoxy-6-oxopyran-2-yl)methyl]cyclohexyl}acetaldehyde

: 631900-31-7
6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1002/anie.200351455

Reference yield:

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

: 631900-31-7
6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

Guidance literature:: Multi-step reaction with 8 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

With pyridine; sodium periodate; osmium(VIII) oxide; tert.-butyl lithium; sodium acetate; pyridinium p-toluenesulfonate; L-Selectride; potassium carbonate; pyridine hydrogenfluoride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; 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

: 631900-31-7
6-[(1R,5S,7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(2-hydroxy-2-phenyl-ethyl)-8-(2-methoxy-ethoxymethoxy)-3,3-dimethyl-2,4-dioxa-bicyclo[3.3.1]non-1-ylmethyl]-4-methoxy-pyran-2-one

Guidance literature:: Multi-step reaction with 4 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

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