2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

Base Information

Chemical Name:2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester
CAS No.:674336-18-6
Molecular Formula:C₃₉H₅₃ClO₇Si₂
Molecular Weight:725.47
Hs Code.:

2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

Synonyms:2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

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Chemical Property of 2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

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Technology Process of 2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

There total 4 articles about 2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid 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: 95.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 674336-17-5
2-(tert-Butyl-diphenyl-silanyloxy)-6-[(2S,4R,6R)-4-(2-chloro-acetoxy)-6-hydroxymethyl-tetrahydro-pyran-2-ylmethyl]-benzoic acid methyl ester

: 674336-18-6
2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃; for 4h;
DOI:10.1021/ja037957x

Reference yield:

: 2-(tert-Butyl-diphenyl-silanyloxy)-6-((2S,4S)-2-methoxymethyl-3,7-dioxa-bicyclo[4.1.0]hept-4-ylmethyl)-benzoic acid methyl ester

: 674336-18-6
2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / DIBAL-H / CH₂Cl₂ / 0.67 h / -78 °C

2: 70 percent / PPh₃; DIAD / toluene / 16 h / 0 - 25 °C

3: 88 percent / 15-crown-5; NaI; BBr₃ / CH₂Cl₂ / 1 h / -30 °C

4: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 - 20 °C

With 2,6-dimethylpyridine; 15-crown-5; di-isopropyl azodicarboxylate; boron tribromide; diisobutylaluminium hydride; triphenylphosphine; sodium iodide; In dichloromethane; toluene; 2: Mitsunobu reaction;
DOI:10.1021/ja037957x

Reference yield:

: 674336-01-7
2-(tert-Butyl-diphenyl-silanyloxy)-6-((2S,4S,6R)-4-hydroxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl)-benzoic acid methyl ester

: 674336-18-6
2-[(2S,4R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(2-chloro-acetoxy)-tetrahydro-pyran-2-ylmethyl]-6-(tert-butyl-diphenyl-silanyloxy)-benzoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / PPh₃; DIAD / toluene / 16 h / 0 - 25 °C

2: 88 percent / 15-crown-5; NaI; BBr₃ / CH₂Cl₂ / 1 h / -30 °C

3: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 - 20 °C

With 2,6-dimethylpyridine; 15-crown-5; di-isopropyl azodicarboxylate; boron tribromide; triphenylphosphine; sodium iodide; In dichloromethane; toluene; 1: Mitsunobu reaction;
DOI:10.1021/ja037957x