Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

Base Information

Chemical Name:Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester
CAS No.:455949-05-0
Molecular Formula:C₆₀H₆₃O₇PSi
Molecular Weight:955.215
Hs Code.:

Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

Synonyms:Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

Chemical Property:

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

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Technology Process of Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

There total 25 articles about Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) 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%

: 197709-11-8
N-[bis(9H-fluoren-9-ylmethoxy)phosphanyl]-N-propan-2-ylpropan-2-amine

: 455948-95-5
(5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

: 455949-05-0
Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

Guidance literature:: N-[bis(9H-fluoren-9-ylmethoxy)phosphanyl]-N-propan-2-ylpropan-2-amine; (5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one; With 1H-tetrazole; In dichloromethane; acetonitrile; at 20 ℃; for 5.5h;

With pyridine; iodine; In tetrahydrofuran; water; at 20 ℃; for 0.0833333h;
DOI:10.1002/chem.200305543

Reference yield:

: 455948-89-7
tert-butyl-[(2S,3S,4S)-3-methoxymethoxy-2,4-dimethyl-hept-6-enyloxy]-dimethylsilane

: 455949-05-0
Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 9-BBN / tetrahydrofuran / 15 h / 20 °C

1.2: 83 percent / aq. NaOH; H₂O₂ / 24 h / 20 °C

2.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

3.1: (i-Pr)2NEt; dibutylboryltriflate / CH₂Cl₂ / 1 h / 0 °C

3.2: CH₂Cl₂ / 3 h / -78 - 20 °C

3.3: 89 percent / aq. H₂O₂ / 1.5 h / 20 °C

4.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 15.5 h / 0 - 20 °C

5.1: Me₃Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

5.2: 84 percent / toluene; tetrahydrofuran / 15.5 h / -20 - 0 °C

6.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 19 h / 0 - 20 °C

7.1: n-BuLi / hexane; tetrahydrofuran / 1.25 h / -78 - 20 °C

7.2: hexane; tetrahydrofuran / 1.25 h / -10 °C

7.3: 2.64 g / aq. disodium tetraborate / methanol / 1.33 h / -10 - 20 °C

8.1: 89 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 1 h / -30 °C

9.1: imidazole / dimethylformamide / 15 h / 20 °C

10.1: 2.43 g / HF/pyridine / tetrahydrofuran / 0.67 h / 20 °C

11.1: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.42 h / 20 °C

12.1: KHMDS; [18]crown-6 / toluene; tetrahydrofuran / 0.58 h / -78 °C

12.2: 2.05 g / toluene; tetrahydrofuran / 4.33 h / -78 °C

13.1: 83 percent / CBr₄ / propan-2-ol / 15 h / 82 °C

14.1: tetrazole / CH₂Cl₂; acetonitrile / 5.5 h / 20 °C

14.2: 95 percent / iodine; pyridine / tetrahydrofuran; H₂O / 0.08 h / 20 °C

With pyridine; 1H-imidazole; 1H-tetrazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; carbon tetrabromide; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; trimethylaluminum; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 2.1: Swern oxidation / 3.1: Evans aldol reaction / 11.1: Dess-Martin oxidation / 12.2: Still-Gennari olefination;
DOI:10.1002/chem.200305543

Reference yield:

: 750646-35-6
(4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-4,6-dimethyl-heptanal

: 455949-05-0
Phosphoric acid (1S,2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-1-[(S)-3-((2S,3S)-3-methyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-butyl]-pent-4-ynyl ester bis-(9H-fluoren-9-ylmethyl) ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: (i-Pr)2NEt; dibutylboryltriflate / CH₂Cl₂ / 1 h / 0 °C

1.2: CH₂Cl₂ / 3 h / -78 - 20 °C

1.3: 89 percent / aq. H₂O₂ / 1.5 h / 20 °C

2.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 15.5 h / 0 - 20 °C

3.1: Me₃Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

3.2: 84 percent / toluene; tetrahydrofuran / 15.5 h / -20 - 0 °C

4.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 19 h / 0 - 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 1.25 h / -78 - 20 °C

5.2: hexane; tetrahydrofuran / 1.25 h / -10 °C

5.3: 2.64 g / aq. disodium tetraborate / methanol / 1.33 h / -10 - 20 °C

6.1: 89 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 1 h / -30 °C

7.1: imidazole / dimethylformamide / 15 h / 20 °C

8.1: 2.43 g / HF/pyridine / tetrahydrofuran / 0.67 h / 20 °C

9.1: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.42 h / 20 °C

10.1: KHMDS; [18]crown-6 / toluene; tetrahydrofuran / 0.58 h / -78 °C

10.2: 2.05 g / toluene; tetrahydrofuran / 4.33 h / -78 °C

11.1: 83 percent / CBr₄ / propan-2-ol / 15 h / 82 °C

12.1: tetrazole / CH₂Cl₂; acetonitrile / 5.5 h / 20 °C

12.2: 95 percent / iodine; pyridine / tetrahydrofuran; H₂O / 0.08 h / 20 °C

With pyridine; 1H-imidazole; 1H-tetrazole; dmap; n-butyllithium; 18-crown-6 ether; carbon tetrabromide; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; trimethylaluminum; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 1.1: Evans aldol reaction / 9.1: Dess-Martin oxidation / 10.2: Still-Gennari olefination;
DOI:10.1002/chem.200305543