4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

Base Information

Chemical Name:4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate
CAS No.:925453-56-1
Molecular Formula:C₄₂H₆₄O₁₄Si₂
Molecular Weight:849.133
Hs Code.:

4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

Synonyms:4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

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Chemical Property of 4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

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Technology Process of 4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

There total 14 articles about 4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate 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: 84.0%

: 644981-60-2
4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R)-3-[(tert-butyldiphenylsilyl)oxymethyl]-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]oct-6-ene-4,5,7-tricarboxylate

: 925453-56-1
4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 3h;
DOI:10.1002/chem.200601212

Reference yield:

: 57992-46-8
3-methoxymethoxy-propionic acid methyl ester

: 925453-56-1
4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 31.4 g / lithium hydroxide monohydrate / tetrahydrofuran; H₂O / 2 h

2: 81 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 20 °C

3: 91 percent / methanol / 0.67 h

4: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

5: 65 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; CH₂Cl₂ / 0.08 h / -93 °C

6: 94 percent / imidazole / tetrahydrofuran / 48 h

7: 78 percent / [Rh₂(OAc)4] bis(methanol) adduct / benzene / 0.42 h / 80 °C

8: 84 percent / OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; acetone / 3 h / 20 °C

With 1H-imidazole; dmap; lithium hydroxide; osmium(VIII) oxide; sodium hexamethyldisilazane; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dirhodium tetraacetate; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene; 4: Dess-Martin oxidation;
DOI:10.1002/chem.200601212

Reference yield:

: 117384-46-0
di-tert-butyl D-tartrate

: 925453-56-1
4,5-di-tert-butyl 7-methyl (1S,3R,4S,5R,6R,7S)-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5,7-tricarboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: Bu₂SnO / toluene / 2 h / Heating

1.2: 92 percent / cesium fluoride / dimethylformamide / 10 h

2.1: LiBH₄ / tetrahydrofuran / 4 h / 20 °C

2.2: 24.5 g / LiBH₄ / tetrahydrofuran / 4 h / -78 °C

3.1: 97 percent / imidazole / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 95 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 5 h

5.1: 96 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer / 2 h / pH 7

6.1: 81 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h / 20 °C

7.1: 91 percent / methanol / 0.67 h

8.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

9.1: 65 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; CH₂Cl₂ / 0.08 h / -93 °C

10.1: 94 percent / imidazole / tetrahydrofuran / 48 h

11.1: 78 percent / [Rh₂(OAc)4] bis(methanol) adduct / benzene / 0.42 h / 80 °C

12.1: 84 percent / OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; acetone / 3 h / 20 °C

With 1H-imidazole; dmap; osmium(VIII) oxide; lithium borohydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; Dess-Martin periodane; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; dirhodium tetraacetate; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 8.1: Dess-Martin oxidation;
DOI:10.1002/chem.200601212