(4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

Base Information

Chemical Name:(4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate
CAS No.:856660-68-9
Molecular Formula:C₄₈H₆₄N₂O₉SSi
Molecular Weight:873.196
Hs Code.:

(4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

Synonyms:(4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

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Chemical Property of (4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

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Technology Process of (4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

There total 14 articles about (4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate 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: 85.0%

: 144090-56-2
2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-4(S)-oxazolidinepropanal

: 856660-63-4
(2S)-benzyl 1-tert-butyldiphenylsilyloxy-5-phenylsulfonylpentan-2-ylcarbamate

: 856660-68-9
(4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: (2S)-benzyl 1-tert-butyldiphenylsilyloxy-5-phenylsulfonylpentan-2-ylcarbamate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

2,2-dimethyl-3-<(1,1-dimethylethoxy)carbonyl>-4(S)-oxazolidinepropanal; In tetrahydrofuran; at -78 ℃; for 1.5h;
DOI:10.3987/COM-04-S(P)40

Reference yield:

: 1155-62-0
N-benzyloxycarbonyl-L-glutamic acid

: 856660-68-9
(4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / BF₃*OEt₂

2: 79 percent / LiBH₄ / methanol; tetrahydrofuran / 4 h / 0 °C

3: 88 percent / pTsOH / CH₂Cl₂ / 24 h / 20 °C

4: 27.4 g / Et₃N / CH₂Cl₂ / 0.5 h / -20 °C

5: tetrahydrofuran / 1 h / 0 - 20 °C

6: 31.4 g / magnesium monoperoxy phthalate / ethanol / 0 °C

7: 24.1 g / CeCl₃*7H₂O; (COOH)2 / acetonitrile / 20 °C

8: 38.6 g / imidazole / dimethylformamide / 2 h / 20 °C

9: 85 percent / nBuLi / tetrahydrofuran; hexane / 2.33 h / -78 - 20 °C

With 1H-imidazole; lithium borohydride; n-butyllithium; cerium(III) chloride; boron trifluoride diethyl etherate; oxalic acid; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200400709

Reference yield:

: 13574-13-5
Boc-Glu(OBzl)-OH

: 856660-68-9
(4S)-tert-butyl 4-(7S)-7-benzyloxycarbonylamino-8-tert-butyldiphenylsilyloxy-3-hydroxy-4-phenylsulfonyloctyl-2,2-dimethyloxazolidine-3-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-hydroxysuccinimide; DCC / ethyl acetate / 20 °C

1.2: 81 percent / NaBH₄ / ethanol; tetrahydrofuran / 0.5 h / 0 °C

2.1: 92 percent / pTsOH / 48 h / 20 °C

3.1: 96 percent / LiAlH₄ / tetrahydrofuran / 0.25 h / 0 °C

4.1: 98 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 2 h / -78 - 20 °C

5.1: 85 percent / nBuLi / tetrahydrofuran; hexane / 2.33 h / -78 - 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 4.1: Swern oxidation;
DOI:10.1002/ejoc.200400709