(2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

Base Information

Chemical Name:(2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester
CAS No.:556038-64-3
Molecular Formula:C₃₈H₄₃Cl₃N₂O₉Si
Molecular Weight:806.212
Hs Code.:

(2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

Synonyms:(2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

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Chemical Property of (2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

There total 23 articles about (2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester 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: 70.0%

: 556038-50-7
(2R,8S)-6-benzyl-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 556038-64-3
(2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

Guidance literature:: With sodium hydrogencarbonate; In acetonitrile; at 70 ℃; for 2h;
DOI:10.1021/ja035303i

Reference yield:

: 20455-07-6
p-nitrophenyl methanesulfonate

: 556038-64-3
(2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: 100 percent / H₂ / Ra-Ni / ethyl acetate; ethanol / 24 h / 23 °C / 72400.7 Torr

2.1: 94.5 g / Br₂ / methanol; CH₂Cl₂ / 0.5 h / 0 - 23 °C

3.1: aq. NaNO₂; H₂SO₄ / acetonitrile / 0 °C

3.2: 96 percent / aq. KI / acetonitrile / 0.75 h

4.1: 100 percent / KOH / CH₂Cl₂; methanol / 0.08 h / 23 °C

5.1: 88 percent / K₂CO₃ / dimethylformamide / 1 h / 23 °C

6.1: n-BuLi / toluene; hexane / -78 °C

6.2: 4.18 g / toluene

7.1: aq. acetic acid / 3 h / 100 °C

8.1: H₅IO₆ / tetrahydrofuran / 0.08 h / 0 °C

9.1: 2.76 percent / NaBH₄ / methanol / 0.08 h / -78 °C

10.1: aq. HCl; Fe; FeCl₂ / ethanol / 2 h / Heating

11.1: 3.42 percent / aq. NaHCO₃ / CH₂Cl₂ / 0.08 h / 23 °C

12.1: K₂CO₃ / dimethylformamide / 1 h / 23 °C

13.1: 1.91 g / PhSH / dimethylformamide / 1 h / 23 °C

14.1: 67 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C

15.1: 100 percent / imidazole / dimethylformamide / 0.17 h / 23 °C

16.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

16.2: 75 percent / toluene; tetrahydrofuran; hexane / 1 h / -78 °C

17.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C

18.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 3 h / 23 °C

19.1: 70 percent / NaHCO₃ / acetonitrile / 2 h / 70 °C

With 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; copper(l) iodide; n-butyllithium; sulfuric acid; hydrogen; bromine; cesium acetate; iron; sodium hydrogencarbonate; potassium carbonate; acetic acid; thiophenol; periodic acid; iron(II) chloride; sodium nitrite; Ra-Ni; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja035303i

Reference yield:

: 37447-35-1
2-benzyloxycarbonylaminomalonic acid dimethyl ester

: 556038-64-3
(2R,8S)-4-benzyloxy-8-(tert-butyldimethylsilanyloxymethyl)-2-methyl-1-oxo-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3,6-tricarboxylic acid 3-benzyl ester 2-methyl ester 6-(2,2,2-trichloroethyl) ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 76 percent / MeONa / methanol / 50 °C

2.1: 4 g / porcine liver lipase / acetone; aq. phosphate buffer / 72 h / 23 °C / pH 7.5 - 8.0

3.1: 100 percent / triphosgene; Et₃N / ethyl acetate / 0.08 h / 0 - 23 °C

4.1: n-BuLi / tetrahydrofuran; hexane / -78 °C

4.2: 75 percent / toluene; tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 82 percent / NBS / dimethylformamide / 0.08 h / 23 °C

6.1: 100 percent / CuI; CsOAc / dimethylsulfoxide / 3 h / 23 °C

7.1: 70 percent / NaHCO₃ / acetonitrile / 2 h / 70 °C

With N-Bromosuccinimide; copper(l) iodide; n-butyllithium; bis(trichloromethyl) carbonate; porcine liver lipase; sodium methylate; cesium acetate; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; phosphate buffer; hexane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/ja035303i