n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

Base Information

Chemical Name:n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside
CAS No.:351011-61-5
Molecular Formula:C₆₄H₇₂O₁₃
Molecular Weight:1049.27
Hs Code.:

Synonyms:n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

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Chemical Property of n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

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Technology Process of n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

There total 10 articles about n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside 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: 66.0%

: 351011-72-8
n-4-pentenyl 2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

: 226919-64-8
dibutyl 2-O-pivaloyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside phosphate

: 351011-61-5
n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 0.666667h;
DOI:10.1021/jo015521z

Reference yield:

: 123826-52-8
p-methoxyphenyl 3,6-di-O-benzyl-α-D-mannopyranoside

: 351011-61-5
n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / pyridine / 0.25 h / -20 °C

2: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h

3: 99 percent / aq. cerium ammonium nitrate / acetonitrile / 0.17 h / 20 °C

4: 70 percent / DBU / CH₂Cl₂ / 0.08 h

5: 76 percent Turnov_. / TBSOTf / CH₂Cl₂ / 1 h / 20 °C

6: 97 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

7: 66 percent / TMSOTf / CH₂Cl₂ / 0.67 h / -78 °C

With pyridine; 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo015521z

Reference yield:

: 98-88-4
benzoyl chloride

: 351011-61-5
n-4-pentenyl 3,4,6-tri-O-benzyl-2-O-pivaloyl-β-D-galactopyranosyl-(1->4)-2-O-benzoyl-3,6-di-O-benzyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / pyridine / 0.25 h / -20 °C

2: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h

3: 99 percent / aq. cerium ammonium nitrate / acetonitrile / 0.17 h / 20 °C

4: 70 percent / DBU / CH₂Cl₂ / 0.08 h

5: 76 percent Turnov_. / TBSOTf / CH₂Cl₂ / 1 h / 20 °C

6: 97 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

7: 66 percent / TMSOTf / CH₂Cl₂ / 0.67 h / -78 °C

With pyridine; 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo015521z