(2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

Base Information

Chemical Name:(2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine
CAS No.:187100-46-5
Molecular Formula:C₄₄H₈₇NO₅SSi₃
Molecular Weight:826.501
Hs Code.:

(2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

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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,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

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Technology Process of (2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

There total 16 articles about (2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine 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:

: (2S,3S,4R,15S,16S)-1,3,15-Tris-tert-butyldimethylsilyloxy-16-methyl-2-p-tolylsulfonylaminooctadecan-4-yl mesylate

: 187100-46-5
(2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

Guidance literature:: With sodium hydride; In tetrahydrofuran;
DOI:10.1016/0040-4039(95)01613-M

Reference yield:

: 764-93-2
1-decyne

: 187100-46-5
(2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

Guidance literature:: Multi-step reaction with 13 steps

1: 53 percent / BuLi, BF₃*Et₂O / hexane; tetrahydrofuran / 1.) -10 deg C, 30 min; -78 deg C, 10 min, 2.) -78 deg C to r.t., 1 h

2: 73 percent / Li, H₂N(CH₂)3NH₂, t-BuOK / 1.) 70 deg C, 2 h; r.t., 15 min, 2.) r.t., 2.5 h

3: 71 percent / Ph₃P, DEAD / tetrahydrofuran / Ambient temperature

4: 86 percent / 1.0 M aq. KOH / tetrahydrofuran; methanol / 5 h

5: 96 percent / imidazole / dimethylformamide / Ambient temperature

6: 94 percent / BuLi / tetrahydrofuran; hexane

7: Li, EtNH₂ / tetrahydrofuran

8: 77 percent / 2,6-dimethylpyridine / CH₂Cl₂ / Ambient temperature

9: 88 percent / pyridine / Ambient temperature

10: 42 percent / 80percent m-CPBA, NaHCO₃ / hexane / Ambient temperature

11: 88 percent / DIBAL / toluene

12: pyridine / 0 °C

13: NaH / tetrahydrofuran / 24 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; potassium hydroxide; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; lithium; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ethylamine; Trimethylenediamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

: 187100-43-2
(2S,3S,4R,5S,15S,16S)-1,3,15-Tris-tert-butyldimethylsilyloxy-4,5-epoxy-16-methyl-2-p-tolylsulfonylaminooctadecane

: 187100-46-5
(2S,3R,4S,11'S,12'S)-3-tert-Butyldimethylsilyloxy-2-tert-butyldimethylsilyloxymethyl-4-(11'-tert-butyldimethylsilyloxy-12'-methyltetradecyl)-N-p-tolylsulfonylazetidine

Guidance literature:: Multi-step reaction with 3 steps

1: 88 percent / DIBAL / toluene

2: pyridine / 0 °C

3: NaH / tetrahydrofuran / 24 h / Ambient temperature

With pyridine; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; toluene;