(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Base Information

Chemical Name:(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene
CAS No.:181267-36-7
Molecular Formula:C₃₁H₅₄O₇Si₂
Molecular Weight:594.937
Hs Code.:

Synonyms:(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

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Chemical Property of (2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

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Technology Process of (2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

There total 16 articles about (2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene 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%

: 181267-34-5
2-[(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl]-ethanol

: 74-88-4
methyl iodide

: 181267-36-7
(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 23 ℃;
DOI:10.1021/ja961230+

Reference yield:

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

: 181267-36-7
(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Guidance literature:: Multi-step reaction with 15 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

12: pyridine, DMAP / dimethylformamide / 3.17 h / 0 - 23 °C

13: AgNO₃, pyridine / dimethylformamide

14: PPTS / methanol; CH₂Cl₂

15: 89 percent / NaH / tetrahydrofuran / 23 °C

With pyridine; 1H-imidazole; chromium dichloride; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; 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

: 181267-36-7
(2R,4aR,6S,7R,8aS,9R,9aR,10aR)-6,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(2-methoxy-ethyl)-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Guidance literature:: Multi-step reaction with 14 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

11: pyridine, DMAP / dimethylformamide / 3.17 h / 0 - 23 °C

12: AgNO₃, pyridine / dimethylformamide

13: PPTS / methanol; CH₂Cl₂

14: 89 percent / NaH / tetrahydrofuran / 23 °C

With pyridine; 1H-imidazole; chromium dichloride; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydride; 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+