(2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

Base Information

Chemical Name:(2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol
CAS No.:942155-72-8
Molecular Formula:C₆₃H₈₅NO₇
Molecular Weight:968.37
Hs Code.:

Synonyms:(2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

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Chemical Property of (2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

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Technology Process of (2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

There total 7 articles about (2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol 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: 76.0%

: 924298-44-2
(1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexan-1-ol

: 800407-54-9
(S)-3-Benzyl-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-[1,2,3]oxathiazolidine 2,2-dioxide

: 942155-72-8
(2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

Guidance literature:: (1S,2S,3S,4S,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexan-1-ol; (S)-3-Benzyl-4-((4S,5R)-2,2-dimethyl-5-tetradecyl-[1,3]dioxolan-4-yl)-[1,2,3]oxathiazolidine 2,2-dioxide; With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 70 ℃; for 20h;

With sulfuric acid; In diethyl ether; at 0 ℃; for 0.25h; Further stages.;
DOI:10.1016/j.tetlet.2007.03.074

Reference yield:

: (3R,4S,5R)-3,4,5-tris(benzyloxy)-2-methoxy-6-methylenetetrahydro-2H-pyran

: 942155-72-8
(2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

Guidance literature:: Multi-step reaction with 7 steps

1.1: H₂O / PdCl₂ / dioxane / 3 h / 60 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

3.1: 88 percent / pyridine / tetrahydrofuran / 1 h / -40 - 20 °C

4.1: BH₃*THF / tetrahydrofuran / 2.5 h / 20 °C

4.2: 76 percent / aq. NaOH; aq. H₂O₂ / 1 h / 0 °C

5.1: NaH; (n-Bu)4NI / dimethylformamide; tetrahydrofuran / 12 h / 20 °C

6.1: TBAF / tetrahydrofuran / 24 h / 20 °C

7.1: NaH / dimethylformamide; tetrahydrofuran / 20 h / 70 °C

7.2: 76 percent / aq.H₂SO₄ / diethyl ether / 0.25 h / 0 °C

With pyridine; 2,6-dimethylpyridine; borane-THF; tetrabutyl ammonium fluoride; water; tetra-(n-butyl)ammonium iodide; sodium hydride; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.03.074

Reference yield:

: 942155-70-6
tert-butyldimethylsilyl 2,3,4-tri-O-benzyl-5a-carba-α-D-galactopyranoside

: 942155-72-8
(2S,3S,4R)-1-O-(2,3,4,6-tetra-O-benzyl-5a-carba-α-D-galactopyranosyl)-2-N-benzylamino-3,4-O-isopropylideneoctadecane-1,3,4-triol

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH; (n-Bu)4NI / dimethylformamide; tetrahydrofuran / 12 h / 20 °C

2.1: TBAF / tetrahydrofuran / 24 h / 20 °C

3.1: NaH / dimethylformamide; tetrahydrofuran / 20 h / 70 °C

3.2: 76 percent / aq.H₂SO₄ / diethyl ether / 0.25 h / 0 °C

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2007.03.074