[(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol

Base Information

Chemical Name:[(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol
CAS No.:213765-39-0
Molecular Formula:C₃₈H₆₃NO₄Si
Molecular Weight:626.008
Hs Code.:

Synonyms:[(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol

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Chemical Property of [(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol

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Technology Process of [(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol

There total 8 articles about [(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol 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: 35.0%

: 213765-18-5
(2R,3S,4S,5R)-3,4-Bis-benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidine

: ((2R,3S,4S,5R)-3,4-Bis-benzyloxy-1-dodecyl-5-hydroxymethyl-pyrrolidin-2-yl)-methanol

: 213765-39-0
[(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(98)01361-6

Reference yield:

: 69-65-8
mannitol

: 213765-39-0
[(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / p-TsOH / dimethylsulfoxide / 16 h / Ambient temperature

2: 61 percent / NaOH, TBAHSO₄ / 22 h / 40 °C

3: 75 percent / AcOH 80percent / H₂O

4: 65 percent / imidazole / dimethylformamide

5: 90 percent / Et₃N / CH₂Cl₂ / 0 °C

6: 70 percent / 18 h / 135 °C

7: 35 percent / TBAF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; sodium hydroxide; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(98)01361-6

Reference yield:

: 36199-02-7
3,4-di-O-benzyl-D-mannitol

: 213765-39-0
[(2R,3S,4S,5R)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-dodecyl-pyrrolidin-2-yl]-methanol

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / imidazole / dimethylformamide

2: 90 percent / Et₃N / CH₂Cl₂ / 0 °C

3: 70 percent / 18 h / 135 °C

4: 35 percent / TBAF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(98)01361-6