2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester
CAS No.:875903-42-7
Molecular Formula:C₅₄H₇₂O₉Si₂
Molecular Weight:921.331
Hs Code.:

2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

Synonyms:2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

There total 12 articles about 2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl 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: 52.0%

: 875903-40-5
2,2-Dimethyl-propionic acid (S)-4-[(3R,4S)-3-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5-oxo-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

: 18295-60-8
propargyl magnesium bromide

: 3282-30-2
pivaloyl chloride

: 875903-41-6
2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5S)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

: 875903-42-7
2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

Guidance literature:: 2,2-Dimethyl-propionic acid (S)-4-[(3R,4S)-3-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-5-oxo-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester; propargyl magnesium bromide; In diethyl ether; toluene; at -78 ℃; for 0.25h;

pivaloyl chloride; With pyridine; dmap; for 17h;
DOI:10.1021/jo052031o

Reference yield:

: 875903-37-0
(4R,5S)-4-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-cyclopent-2-enone

: 875903-42-7
2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 51 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / -65 °C

2.1: 81 percent / pyridine; iodine / tetrahydrofuran / 0.5 h / 20 °C

3.1: 97 percent / CuI; ethyldiisopropylamine / (Ph₃P)4Pd / dimethylformamide / 1 h / 20 °C

4.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / -70 °C

5.1: toluene; diethyl ether / 0.25 h / -78 °C

5.2: 44 percent / pyridine; DMAP / 17 h

With pyridine; 2,6-dimethylpyridine; copper(l) iodide; boron trifluoride diethyl etherate; iodine; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Sonogashira coupling;
DOI:10.1021/jo052031o

Reference yield:

: 875903-39-2
2,2-Dimethyl-propionic acid (S)-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-hydroxy-but-3-ynyl ester

: 875903-42-7
2,2-Dimethyl-propionic acid (S)-4-[(3R,4S,5R)-3-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-(4-methoxy-benzyloxy)-5-prop-2-ynyl-cyclopent-1-enyl]-2-(R)-1,4-dioxa-spiro[4.4]non-2-yl-2-triethylsilanyloxy-but-3-ynyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 97 percent / CuI; ethyldiisopropylamine / (Ph₃P)4Pd / dimethylformamide / 1 h / 20 °C

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / -70 °C

3.1: toluene; diethyl ether / 0.25 h / -78 °C

3.2: 44 percent / pyridine; DMAP / 17 h

With 2,6-dimethylpyridine; copper(l) iodide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Sonogashira coupling;
DOI:10.1021/jo052031o