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

Base Information

Chemical Name:di-tert-butyl (1S,3R,4S,5R,6R,7R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate
CAS No.:644981-47-5
Molecular Formula:C₄₂H₆₄O₁₃Si₂
Molecular Weight:833.133
Hs Code.:

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

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

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

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

There total 13 articles about di-tert-butyl (1S,3R,4S,5R,6R,7R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate 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: 88.0%

: 644981-46-4
di-tert-butyl (1S,3R,4S,5R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-1-[2(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]oct-6-ene-4,5-dicarboxylate

: 644981-47-5
di-tert-butyl (1S,3R,4S,5R,6R,7R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 20h;
DOI:10.1002/anie.200352629

Reference yield:

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

: 644981-47-5
di-tert-butyl (1S,3R,4S,5R,6R,7R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: Bu₂SnO / toluene / 2 h / Heating

1.2: 92 percent / CsF / dimethylformamide / 10 h

2.1: LiBH₄ / tetrahydrofuran / 4 h

2.2: water / tetrahydrofuran

2.3: 72 percent / 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; H₂O / 2 h / pH 7

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

7.1: 91 percent / TsOH / methanol / 0.67 h

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

9.1: 65 percent / NaHMDS / CH₂Cl₂; tetrahydrofuran / 0.08 h / -93 °C

10.1: 94 percent / imidazole / tetrahydrofuran / 48 h

11.1: 72 percent / Rh₂(OAc)4 / benzene / 1 h / Heating

12.1: 88 percent / OsO₄; 4-methylmorpholine N-oxide / acetone; H₂O / 20 h

With 1H-imidazole; dmap; dirhodium tetraacetate; osmium(VIII) oxide; lithium borohydride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; di(n-butyl)tin oxide; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; benzene;
DOI:10.1002/anie.200352629

Reference yield:

: 207124-07-0
3-(methoxymethoxy)propionic acid

: 644981-47-5
di-tert-butyl (1S,3R,4S,5R,6R,7R)-7-acetyl-3-[(tert-butyldiphenylsilyl)oxymethyl]-6,7-dihydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Guidance literature:: Multi-step reaction with 7 steps

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

2: 91 percent / TsOH / methanol / 0.67 h

3: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

4: 65 percent / NaHMDS / CH₂Cl₂; tetrahydrofuran / 0.08 h / -93 °C

5: 94 percent / imidazole / tetrahydrofuran / 48 h

6: 72 percent / Rh₂(OAc)4 / benzene / 1 h / Heating

7: 88 percent / OsO₄; 4-methylmorpholine N-oxide / acetone; H₂O / 20 h

With 1H-imidazole; dmap; dirhodium tetraacetate; osmium(VIII) oxide; sodium hexamethyldisilazane; Dess-Martin periodane; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; water; acetone; benzene;
DOI:10.1002/anie.200352629