(2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

Base Information

Chemical Name:(2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester
CAS No.:556038-67-6
Molecular Formula:C₄₂H₄₁N₃O₁₃S
Molecular Weight:827.866
Hs Code.:

(2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

Synonyms:(2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

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Chemical Property of (2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

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Technology Process of (2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

There total 33 articles about (2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl 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: 88.0%

: 124-63-0
methanesulfonyl chloride

: 556038-66-5
(2R,8S)-4-benzyloxy-8-hydroxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

: 556038-67-6
(2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

Guidance literature:: With pyridine; at 23 ℃; for 0.166667h;
DOI:10.1021/ja035303i

Reference yield:

: 35274-53-4
2-bromo-3,4,5-tri-methoxybenzaldehyde

: 556038-67-6
(2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 97 percent / 1,1,3,3-tetramethylguanidine / CH₂Cl₂ / 48 h / 23 °C

2: 98 percent / CuI; CsOAc / dimethylsulfoxide / 24 h / 23 °C

3: 99 percent / H₂ / Pd/C / ethyl acetate; ethanol / 3 h / 23 °C

4: 89 percent / aq. KOH / methanol / 1 h / Heating

5: SOCl₂; DMF / toluene / 0.33 h / 70 °C

6: 68.5 mg / pyridine; CH₂Cl₂ / 0.17 h / 0 °C

7: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C

8: 88 percent / pyridine / 0.17 h / 23 °C

With pyridine; potassium hydroxide; copper(l) iodide; thionyl chloride; tetrabutyl ammonium fluoride; hydrogen; cesium acetate; N,N-dimethyl-formamide; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; 1: Horner-Wadsworth-Emmon reaction;
DOI:10.1021/ja035303i

Reference yield:

: 20455-07-6
p-nitrophenyl methanesulfonate

: 556038-67-6
(2R,8S)-4-benzyloxy-8-methanesulfonyloxymethyl-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2,3-dicarboxylic acid 3-benzyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 23 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

20.1: 69 percent / Zn; aq. KH₂PO₄ / tetrahydrofuran / 1 h / 23 °C

21.1: 68.5 mg / pyridine; CH₂Cl₂ / 0.17 h / 0 °C

22.1: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.5 h / 23 °C

23.1: 88 percent / pyridine / 0.17 h / 23 °C

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