(S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol

Base Information

Chemical Name:(S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol
CAS No.:129077-29-8
Molecular Formula:C₂₇H₃₁NO₄
Molecular Weight:433.547
Hs Code.:

Synonyms:(S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol

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Chemical Property of (S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol

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Technology Process of (S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol

There total 16 articles about (S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol 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: 65.0%

: 129077-19-6
(2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-2-vinyl-pyrrolidine

: 129077-29-8
(S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; water; In 1,4-dioxane; at 60 ℃;
DOI:10.1055/s-2001-14593

Reference yield: 61.0%

: 129077-19-6
(2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-2-vinyl-pyrrolidine

: 129101-81-1
(S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-1-oxy-pyrrolidin-2-yl)-ethane-1,2-diol

: 129077-29-8
(S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In 1,4-dioxane; water; for 24h; Ambient temperature;
DOI:10.1016/0040-4039(90)87010-W

Reference yield:

: 100-46-9
benzylamine

: 129077-29-8
(S)-1-((2R,3S,4S)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidin-2-yl)-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: molecular sieves 4 Angstroem / diethyl ether / 20 °C

2.1: Et₂O*BF₃ / -78 - -40 °C

2.2: tetrahydrofuran; diethyl ether / -78 - 20 °C

3.1: 90 percent / pyridine; H₂O / tetrahydrofuran / 20 °C

4.1: 85 percent / NaH; Bu₄NI / tetrahydrofuran / 20 °C

5.1: 85 percent / TBAF supported on SiO₂ / tetrahydrofuran / 20 °C

6.1: 95 percent / aq. LiOH / dioxane / Heating

7.1: 73 percent / Ph₃P; CCl₄; Et₃N / dimethylformamide / 20 °C

8.1: 85 percent / NaH; Bu₄NI / tetrahydrofuran / 20 °C

9.1: 65 percent / NMO; OsO₄; H₂O / dioxane / 60 °C

With pyridine; tetrachloromethane; lithium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1055/s-2001-14593