(2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal

Base Information

Chemical Name:(2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal
CAS No.:916321-44-3
Molecular Formula:C₃₈H₆₈O₇Si₂
Molecular Weight:693.125
Hs Code.:

Synonyms:(2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal

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Chemical Property of (2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal

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Technology Process of (2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal

There total 16 articles about (2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal 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: 99.0%

: 916321-43-2
(2R,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanol

: 916321-44-3
(2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal

Guidance literature:: With N-methyl-2-indolinone; tetrapropylammonium perruthennate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ol062058+

Reference yield:

: 916321-09-0
S-ethyll (2S,3S,4R)-4-(tert-butyldimethylsiloxy)-3-hydroxy-2-methylpentanethioate

: 916321-44-3
(2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal

Guidance literature:: Multi-step reaction with 13 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2.1: 100 percent / Et₃SiH / Pd/C / acetone / 1.5 h / 0 °C

3.1: 95 percent / toluene / 6.5 h / 100 °C

4.1: 92 percent / L-Selectride(R) / tetrahydrofuran / 5 h / 20 °C

5.1: 100 percent / NMO; TPAP / CH₂Cl₂ / 2 h / 0 °C

6.1: 49.9 percent / tetrahydrofuran / 3 h / -78 °C

7.1: 96 percent / iPr₂NEt / CH₂Cl₂ / 11 h / 60 °C

8.1: 92 percent / Red-Al(R) / toluene / 2 h / 0 °C

9.1: 93 percent / DMAP; pyridine / 1 h / 0 °C

10.1: OsO₄ / pyridine / 48 h / 0 °C

10.2: 30 percent / H₂S / tetrahydrofuran; hexane

11.1: 97 percent / CSA / CH₂Cl₂ / 8 h / 20 °C

12.1: 90 percent / K₂CO₃ / methanol / 12 h / 20 °C

13.1: 99 percent / NMO; TPAP / CH₂Cl₂ / 1 h / 0 °C

With pyridine; 2,6-dimethylpyridine; triethylsilane; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; camphor-10-sulfonic acid; L-Selectride; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; toluene; 3.1: Wittig reaction;
DOI:10.1021/ol062058+

Reference yield:

: 916321-31-8
S-ethyll (2S,3S,4R)-3,4-di(tert-butyldimethylsiloxy)-2-methylpentanethioate

: 916321-44-3
(2S,3R,4R,5R,6R,7S,8R)-3-(benzyloxymethoxy)-7,8-di(tert-butyldimethylsiloxy)-4,5-(cyclohexylidenedioxy)-2,4,6-trimethylnonanal

Guidance literature:: Multi-step reaction with 12 steps

1.1: 100 percent / Et₃SiH / Pd/C / acetone / 1.5 h / 0 °C

2.1: 95 percent / toluene / 6.5 h / 100 °C

3.1: 92 percent / L-Selectride(R) / tetrahydrofuran / 5 h / 20 °C

4.1: 100 percent / NMO; TPAP / CH₂Cl₂ / 2 h / 0 °C

5.1: 49.9 percent / tetrahydrofuran / 3 h / -78 °C

6.1: 96 percent / iPr₂NEt / CH₂Cl₂ / 11 h / 60 °C

7.1: 92 percent / Red-Al(R) / toluene / 2 h / 0 °C

8.1: 93 percent / DMAP; pyridine / 1 h / 0 °C

9.1: OsO₄ / pyridine / 48 h / 0 °C

9.2: 30 percent / H₂S / tetrahydrofuran; hexane

10.1: 97 percent / CSA / CH₂Cl₂ / 8 h / 20 °C

11.1: 90 percent / K₂CO₃ / methanol / 12 h / 20 °C

12.1: 99 percent / NMO; TPAP / CH₂Cl₂ / 1 h / 0 °C

With pyridine; triethylsilane; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; camphor-10-sulfonic acid; L-Selectride; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; toluene; 2.1: Wittig reaction;
DOI:10.1021/ol062058+