(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:153277-27-1
Molecular Formula:C₂₉H₄₈N₂O₇Si
Molecular Weight:564.795
Hs Code.:

(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl 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 (2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

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

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Technology Process of (2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 17 articles about (2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl 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: 97.0%

: 153277-26-0
(2S,3S,1'S,2'R,3'R)-1-(tert-Butoxycarbonyl)-2-<3'-benzyloxycarbonylamine-4'-(tert-butyldimethylsilyloxy)-1'-hydroxy-2'-phenylsulfonylbutyl>-3-(methoxymethoxy)pyrrolidine

: 153277-27-1
(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With potassium dihydrogenphosphate; sodium amalgam; In methanol; at 0 - 20 ℃; for 18h;

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 153277-27-1
(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / DMAP, pyridine / CH₂Cl₂ / 16 h / -18 °C

2: 98 percent / NaH / dimethylformamide / 1.) 10 min, 2.) 20 deg C, 16 h

3: 97 percent / NaBH₄ / methanol / 5 h / 20 °C

4: 92 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / 20 °C

5: 87 percent / MCPBA / CH₂Cl₂ / 1.) ice-cooling, 0.5 h, 2.) 20 deg C, 2 h

6: 60 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h

7: 97 percent / Na, KH₂PO₄ / methanol / 18 h / 0 - 20 °C

With pyridine; dmap; sodium tetrahydroborate; potassium dihydrogenphosphate; n-butyllithium; sodium amalgam; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 130948-04-8
Methyl 1-(tert-butoxycarbonyl)-3-oxopyrrolidine-2-carboxylate

: 153277-27-1
(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 61 percent / sugar / H₂O / 24 h / 34 °C / Baker's yeast

2: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 15 h / 20 °C

3: 71 percent / BF₃*Et₂O, diisobutylaluminium hydride / toluene / 1.) -78 deg C, 1 h, 2.) r.t., 4 h

4: 79 percent / TPAP, N-methylmorpholine N-oxide, molecular sieves / CH₂Cl₂; acetonitrile / 18 h / Ambient temperature

5: 60 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h

6: 97 percent / Na, KH₂PO₄ / methanol / 18 h / 0 - 20 °C

With potassium dihydrogenphosphate; n-butyllithium; molecular sieve; tetrapropylammonium perruthennate; sodium amalgam; boron trifluoride diethyl etherate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; Sucrose; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile;