(S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Base Information

Chemical Name:(S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester
CAS No.:159153-49-8
Molecular Formula:C₃₃H₅₄O₇Si
Molecular Weight:590.873
Hs Code.:

(S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Synonyms:(S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

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Chemical Property of (S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

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Technology Process of (S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

There total 77 articles about (S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl 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: 93.0%

: 159153-48-7
(S)-2-((2S,5R)-5-((R)-2-(tert-butyldimethylsiloxy)propyl)tetrahydrofuran-2-yl)propanoic acid

: 58106-10-8
(R)-benzyl 2-((2R,5S)-5-((S)-2-hydroxypropyl)tetrahydrofuran-2-yl)propanoate

: 159153-49-8
(S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 15h; Ambient temperature;
DOI:10.1039/c39940002287

Reference yield: 63.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: (S)-2-[(2S,5R)-5-((R)-2-Hydroxy-propyl)-tetrahydro-furan-2-yl]-propionic acid 2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

: 159153-49-8
(S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 0.25h;
DOI:10.1016/0040-4020(95)00913-2

Reference yield:

: 133774-88-6
4-(5'-<(5S)-3-methyl-5-oxomethyl-4,5-dihydroisoxazolyl>)(7R)-10,10-dimethyl-5-thia-4-azatricyclo<5.2.1.0^3,7>decane 5,5-dioxide

: 159153-49-8
(S)-2-{(2S,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-propyl]-tetrahydro-furan-2-yl}-propionic acid (S)-2-[(2S,5R)-5-((R)-1-benzyloxycarbonyl-ethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 91 percent / L-selectride / tetrahydrofuran / 0.33 h / Ambient temperature

2: 95 percent / iodine, triphenylphosphine, imidazole / diethyl ether; acetonitrile / 10.5 h / Ambient temperature

3: 1.) NaH, n-BuLi / 1.) THF, HMPA, hexane, 25 min, 2.) THF, HMPA, hexane, 10 min

4: boric acid, H₂ / Ra-Ni / methanol; H₂O / 21 h

5: oxalic acid / CH₂Cl₂ / 2 h / Heating

6: 95 percent / L-selectride / tetrahydrofuran / 0.17 h / -78 °C

7: 62 percent / H₂ / 5percent Rh/Al₂O₃ / methanol / 120 h / 3620.04 Torr

8: 92 percent / triphenylphosphine, DEAD / tetrahydrofuran / 17 h

9: 100 percent / 2N aq. NaOH / methanol / 11 h

10: 1.) potassium tert-butoxide / 1.) DMF, 40 min, 2.) DMF, 60-70 deg C, 19 h 20 min

11: 63 percent / imidazole, DMAP / dimethylformamide / 0.25 h

With 1H-imidazole; dmap; sodium hydroxide; n-butyllithium; potassium tert-butylate; hydrogen; iodine; boric acid; oxalic acid; L-Selectride; sodium hydride; triphenylphosphine; diethylazodicarboxylate; Rh/Al₂O₃; Ra-Ni; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0040-4020(95)00913-2