Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester

Base Information

Chemical Name:Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester
CAS No.:853193-46-1
Molecular Formula:C₃₇H₄₃BrO₄
Molecular Weight:631.65
Hs Code.:

Synonyms:Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester

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Chemical Property of Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester

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Technology Process of Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester

There total 14 articles about Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl 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%

: 853193-71-2
(1S,4aR,7S,8S,8aS)-8-((R)-3-Hydroxy-5-trityloxy-pentyl)-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol

: 598-21-0
2-Bromoacetyl bromide

: 853193-46-1
Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester

Guidance literature:: With pyridine; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ja043506g

Reference yield:

: 853193-65-4
(R)-4-But-3-ynyl-2,2-dimethyl-[1,3]dioxane

: 853193-46-1
Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 68 percent / oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

3.1: 93 percent / amberlyst 15; water / tetrahydrofuran / 24 h / 20 °C

4.1: 79 percent / imidazole / CH₂Cl₂ / 1.33 h / 20 °C

5.1: 85 percent / H₂; quinoline / Lindlar catalyst / hexane / 0.5 h / 20 °C

6.1: Al(OTf)3; TfOH / CH₂Cl₂ / 72 h / -20 °C

6.2: aq. HCl / tetrahydrofuran / 45 °C

6.3: K₂CO₃ / methanol / 2 h / 20 °C

7.1: 84 percent / pyridine / 3 h / 20 °C

8.1: 96 percent / L-selectride / tetrahydrofuran / -78 - 20 °C

9.1: 88 percent / pyridine / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 1H-imidazole; quinoline; aluminium(III) triflate; n-butyllithium; Amberlyst 15; oxalyl dichloride; trifluorormethanesulfonic acid; water; hydrogen; L-Selectride; dimethyl sulfoxide; triethylamine; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; 2.1: Swern oxidation / 6.1: intermolecular Diels-Alder reaction;
DOI:10.1021/ja043506g

Reference yield:

: 853193-64-3
Toluene-4-sulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester

: 853193-46-1
Bromo-acetic acid (R)-1-[2-((1S,2S,4aR,8S,8aS)-8-hydroxy-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-ethyl]-3-trityloxy-propyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 89 percent / dimethylsulfoxide / 0.17 h / cooling

2.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 68 percent / oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

4.1: 93 percent / amberlyst 15; water / tetrahydrofuran / 24 h / 20 °C

5.1: 79 percent / imidazole / CH₂Cl₂ / 1.33 h / 20 °C

6.1: 85 percent / H₂; quinoline / Lindlar catalyst / hexane / 0.5 h / 20 °C

7.1: Al(OTf)3; TfOH / CH₂Cl₂ / 72 h / -20 °C

7.2: aq. HCl / tetrahydrofuran / 45 °C

7.3: K₂CO₃ / methanol / 2 h / 20 °C

8.1: 84 percent / pyridine / 3 h / 20 °C

9.1: 96 percent / L-selectride / tetrahydrofuran / -78 - 20 °C

10.1: 88 percent / pyridine / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 1H-imidazole; quinoline; aluminium(III) triflate; n-butyllithium; Amberlyst 15; oxalyl dichloride; trifluorormethanesulfonic acid; water; hydrogen; L-Selectride; dimethyl sulfoxide; triethylamine; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 3.1: Swern oxidation / 7.1: intermolecular Diels-Alder reaction;
DOI:10.1021/ja043506g