benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

Base Information

Chemical Name:benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate
CAS No.:878807-62-6
Molecular Formula:C₃₅H₄₈N₂O₇Si
Molecular Weight:636.861
Hs Code.:

benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

Synonyms:benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

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Chemical Property of benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

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Technology Process of benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

There total 9 articles about benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate 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: 54.0%

: 878807-61-5
benzyl [(1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

: 69739-34-0
t-butyldimethylsiyl triflate

: 878807-62-6
benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

Guidance literature:: With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; In dichloromethane; at 20 ℃; for 0.333333h;
DOI:10.1016/j.tetasy.2005.10.040

Reference yield:

: 496-15-1
1-indoline

: 878807-62-6
benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 84 percent / CuCl; triethylamine / tetrahydrofuran / 3.5 h / Heating

2.1: 86 percent / H₂; quinoline / Lindlar's catalyst / methanol / 0.5 h / 20 °C / 2327.17 Torr

3.1: 84 percent / MnO₂ / toluene / 72 h / Heating

4.1: 87 percent / N-iodosuccinimide / dimethylformamide / 0.33 h / 0 °C

5.1: K₂[OsO₂(OH)4]; (DHQD)2PYR; K₃[Fe(CN)6] / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 20 °C

6.1: TsCl; triethylamine; Me₃N*HCl / CH₂Cl₂ / 0.33 h / 0 °C

6.2: 84 percent / K₂CO₃ / CH₂Cl₂; methanol / 24 h / 20 °C

7.1: BuLi / diethyl ether; hexane / 1 h / -78 °C

7.2: MgBr₂ / diethyl ether / -78 - 0 °C

7.3: 21 percent / CH₂Cl₂; diethyl ether / 0.5 h / 0 °C

8.1: 54 percent / Proton Sponge(R) / CH₂Cl₂ / 0.33 h / 20 °C

With quinoline; manganese(IV) oxide; N-iodo-succinimide; n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; K2; hydrogen; trimethylamine hydrochloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; triethylamine; p-toluenesulfonyl chloride; copper(l) chloride; potassium hexacyanoferrate(III); Lindlar's catalyst; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5.1: Sharpless dihydroxylation / 7.3: Grignard reaction;
DOI:10.1016/j.tetasy.2005.10.040

Reference yield:

: 878807-58-0
3-iodo-1-(2-methylbut-3-en-2-yl)-1H-indole

: 878807-62-6
benzyl [(1S,2R)-2-(tert-butyldimethylsilyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-2-(1-{2-[(R)-oxiran-2-yl]propan-2-yl}-1H-indol-3-yl)ethyl]carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: K₂[OsO₂(OH)4]; (DHQD)2PYR; K₃[Fe(CN)6] / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 20 °C

2.1: TsCl; triethylamine; Me₃N*HCl / CH₂Cl₂ / 0.33 h / 0 °C

2.2: 84 percent / K₂CO₃ / CH₂Cl₂; methanol / 24 h / 20 °C

3.1: BuLi / diethyl ether; hexane / 1 h / -78 °C

3.2: MgBr₂ / diethyl ether / -78 - 0 °C

3.3: 21 percent / CH₂Cl₂; diethyl ether / 0.5 h / 0 °C

4.1: 54 percent / Proton Sponge(R) / CH₂Cl₂ / 0.33 h / 20 °C

With n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; K2; trimethylamine hydrochloride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; triethylamine; p-toluenesulfonyl chloride; potassium hexacyanoferrate(III); potassium carbonate; In diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; 1.1: Sharpless dihydroxylation / 3.3: Grignard reaction;
DOI:10.1016/j.tetasy.2005.10.040