(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

Base Information

Chemical Name:(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol
CAS No.:181267-32-3
Molecular Formula:C₂₄H₃₈O₇Si
Molecular Weight:466.647
Hs Code.:

Synonyms:(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

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Chemical Property of (2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

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Technology Process of (2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

There total 12 articles about (2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol 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%

: [(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6-Acetoxy-9-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-acetic acid methyl ester

: 181267-32-3
(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; at -78 - 23 ℃; for 1.16667h;
DOI:10.1021/ja961230+

Reference yield:

: 82659-53-8
(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene

: 181267-32-3
(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

Guidance literature:: Multi-step reaction with 11 steps

1: K₂CO₃ / methanol / 12 h / 23 °C

2: CSA / dimethylformamide / 2 h / 50 °C

3: 90 percent / AgNO₃, pyridine / dimethylformamide / 4 h / 23 °C

4: OsO₄, NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O

5: NaIO₄ / methanol

6: NiCl₂/CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 23 °C

7: 91 percent / pyridine

8: n-Bu₄NF, imidazole / tetrahydrofuran

9: DBU / CH₂Cl₂

10: 83 percent / i-Pr₂NEt / CH₂Cl₂

11: 90 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

With pyridine; 1H-imidazole; chromium dichloride; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja961230+

Reference yield:

: 106756-74-5
(2R,3R,4R,5S,6R)-2-allyl-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

: 181267-32-3
(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxy)-7-(2-hydroxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

Guidance literature:: Multi-step reaction with 10 steps

1: CSA / dimethylformamide / 2 h / 50 °C

2: 90 percent / AgNO₃, pyridine / dimethylformamide / 4 h / 23 °C

3: OsO₄, NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O

4: NaIO₄ / methanol

5: NiCl₂/CrCl₂ / tetrahydrofuran; dimethylsulfoxide / 23 °C

6: 91 percent / pyridine

7: n-Bu₄NF, imidazole / tetrahydrofuran

8: DBU / CH₂Cl₂

9: 83 percent / i-Pr₂NEt / CH₂Cl₂

10: 90 percent / DIBAL / diethyl ether / 1.17 h / -78 - 23 °C

With pyridine; 1H-imidazole; chromium dichloride; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; nickel dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja961230+