(E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

Base Information

Chemical Name:(E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside
CAS No.:195147-49-0
Molecular Formula:C₃₁H₃₅FO₅
Molecular Weight:506.614
Hs Code.:

Synonyms:(E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

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Chemical Property of (E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

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Technology Process of (E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

There total 6 articles about (E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside 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: 74.0%

: 195147-47-8
(R/S)-but-3-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

: 195147-49-0
(E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

Guidance literature:: With n-butyllithium; Wilkinson's catalyst; In tetrahydrofuran; for 0.5h; Heating;
DOI:10.1039/a701630a

Reference yield:

: 200396-09-4
((Ξ)-1-methyl-allyl)-β-D-glucopyranoside

: 195147-49-0
(E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: CSA / acetonitrile / 2 h

2: 99 percent / NaH / dimethylformamide / 3 h / 0 °C

3: 70 percent / Et₃SiH, TFA / CH₂Cl₂ / 2 h / Ambient temperature

4: pyridine / CH₂Cl₂ / 0.67 h / Ambient temperature

5: 70 percent / TBAF / tetrahydrofuran

6: 74 percent / BuLi / Rh(PPh₃)3Cl / tetrahydrofuran / 0.5 h / Heating

With pyridine; triethylsilane; n-butyllithium; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; trifluoroacetic acid; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/a701630a

Reference yield:

: 157477-49-1
(R/S)-but-3-en-2-yl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

: 195147-49-0
(E/Z)-but-2-en-2-yl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: t-BuOK / methanol / 3.5 h / Ambient temperature

2: CSA / acetonitrile / 2 h

3: 99 percent / NaH / dimethylformamide / 3 h / 0 °C

4: 70 percent / Et₃SiH, TFA / CH₂Cl₂ / 2 h / Ambient temperature

5: pyridine / CH₂Cl₂ / 0.67 h / Ambient temperature

6: 70 percent / TBAF / tetrahydrofuran

7: 74 percent / BuLi / Rh(PPh₃)3Cl / tetrahydrofuran / 0.5 h / Heating

With pyridine; triethylsilane; n-butyllithium; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; trifluoroacetic acid; Wilkinson's catalyst; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/a701630a