(2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

Base Information

Chemical Name:(2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane
CAS No.:943144-54-5
Molecular Formula:C₄₈H₆₆O₈Si₂
Molecular Weight:827.218
Hs Code.:

(2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

Synonyms:(2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

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Chemical Property of (2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

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Technology Process of (2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

There total 9 articles about (2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane 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: 100.0%

: 943144-68-1
(2R,4R,5R)-5-benzoyloxymethyl-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)-2-heptanol

: 69739-34-0
t-butyldimethylsiyl triflate

: 943144-54-5
(2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1016/j.tetlet.2007.03.152 DOI:10.1021/jo8005599

Reference yield:

: 943144-61-4
(3E)-3-[(3R)-3,4-isopropylidenedioxybutylidene]-2-tetrahydrofuran

: 943144-54-5
(2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

Guidance literature:: Multi-step reaction with 9 steps

1.1: DIBAlH / toluene / 0.33 h / -78 °C

2.1: imidazole / dimethylformamide / 0.5 h / 20 °C

3.1: NaBH₄; CeCl₃*7H₂O / methanol / 0.25 h / -78 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 91 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; MeSO₂NH₂ / K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

6.1: p-TsOH*H₂O / 0.33 h / 20 °C

7.1: Zn(NO₃)2*6H₂O / acetonitrile / 3 h / 50 °C

8.1: n-Bu₂SnO / toluene / 12 h / Heating

8.2: 76 percent / n-Bu₄NI / toluene / 1.5 h / Heating

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; zinc(II) nitrate; sodium tetrahydroborate; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium carbonate; potassium hexacyanoferrate(III); In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2007.03.152

Reference yield:

: 943144-62-5
C₁₁H₁₈O₄

: 943144-54-5
(2R,4R,5R)-5-benzoyloxymethyl-2-tert-butyldimethylsiloxy-7-tert-butyldiphenylsiloxy-4,5-isopropylidenedioxy-1-(4-methoxybenzyloxy)heptane

Guidance literature:: Multi-step reaction with 8 steps

1.1: imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: NaBH₄; CeCl₃*7H₂O / methanol / 0.25 h / -78 °C

3.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 91 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; MeSO₂NH₂ / K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

5.1: p-TsOH*H₂O / 0.33 h / 20 °C

6.1: Zn(NO₃)2*6H₂O / acetonitrile / 3 h / 50 °C

7.1: n-Bu₂SnO / toluene / 12 h / Heating

7.2: 76 percent / n-Bu₄NI / toluene / 1.5 h / Heating

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; zinc(II) nitrate; sodium tetrahydroborate; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium carbonate; potassium hexacyanoferrate(III); In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 4.1: Sharpless asymmetric dihydroxylation;
DOI:10.1016/j.tetlet.2007.03.152