di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Base Information

Chemical Name:di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate
CAS No.:644981-52-2
Molecular Formula:C₃₃H₅₀O₁₄
Molecular Weight:670.752
Hs Code.:

di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Synonyms:di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-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)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-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)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

There total 21 articles about di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-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: 97.0%

: 644981-51-1
di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-3-[(tert-butyldiphenylsilyl)oxymethyl]-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

: 644981-52-2
di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1002/anie.200352629 DOI:10.1002/chem.200601212

Reference yield:

: 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

: 644981-52-2
di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 88 percent / OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; H₂O; acetone / 3 h / 20 °C

2: 95 percent / Ag₂O / dimethylformamide / 24 h

3: 100 percent / diisobutylaluminum hydride / toluene / 0.5 h / -78 °C

4: 94 percent / [Pb(OAC)4] / benzene / 0.5 h

5: 85 percent / diisobutylaluminum hydride; ZnCl₂ / CH₂Cl₂ / 0.5 h / -78 °C

6: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

7: 97 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 0 °C

With dmap; osmium(VIII) oxide; tetrabutyl ammonium fluoride; lead(IV) tetraacetate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; zinc(II) chloride; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1002/chem.200601212

Reference yield:

: 644981-50-0
di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-3-[(tert-butyldiphenylsilyl)oxymethyl]-7-hydroxy-1-[2-(methoxymethoxy)ethyl]-4-(trimethylsilyl)oxy-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

: 644981-52-2
di-tert-butyl (1S,3R,4S,5R,6R,7R)-6-benzyloxy-7-(tert-butoxycarbonyl)oxy-4-hydroxy-3-(hydroxymethyl)-1-[2-(methoxymethoxy)ethyl]-2,8-dioxabicyclo[3.2.1]octane-4,5-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 97 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 0 °C

With dmap; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200601212