6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside

Base Information

Chemical Name:6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside
CAS No.:351011-67-1
Molecular Formula:C₇₃H₈₅NO₁₄
Molecular Weight:1200.48
Hs Code.:

Synonyms:6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside

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Chemical Property of 6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside

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Technology Process of 6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside

There total 6 articles about 6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-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: 54.0%

: 17996-12-2
N-benzyloxycarbonyl-6-amino-1-hexanol

: 351011-51-3
ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-thio-β-D-mannopyranoside

: 351011-67-1
6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside

Guidance literature:: N-benzyloxycarbonyl-6-amino-1-hexanol; ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-thio-β-D-mannopyranoside; With 4 A molecular sieve; Di-tert-butylpyridine; In dichloromethane; at 20 ℃; for 0.5h;

With methyl trifluoromethanesulfonate; at 0 ℃; for 20h; Further stages.;
DOI:10.1021/jo015521z

Reference yield:

: 3282-30-2
pivaloyl chloride

: 351011-67-1
6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: DMAP / CH₂Cl₂ / 0.5 h

1.2: 95 percent / 1 h / 20 °C

2.1: 4A molecular sieves; di-tert-butylpyridine / CH₂Cl₂ / 0.5 h / 20 °C

2.2: 54 percent / MeOTf / 20 h / 0 °C

With dmap; 4 A molecular sieve; Di-tert-butylpyridine; In dichloromethane;
DOI:10.1021/jo015521z

Reference yield:

: 114117-12-3
2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-1,5-anhydro-2-deoxy-3,6-di-O-benzyl-D-arabino-hex-1-enitol

: 351011-67-1
6-(benzyloxycarbonylamino)hexyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,2'-dimethyldioxirane / CH₂Cl₂; acetone / 0.17 h / 0 °C

2.1: 143 mg / trifluoroacetic anhydride / CH₂Cl₂ / 16 h / -78 - 20 °C

3.1: Ac₂O; DMSO / 72 h / 20 °C

3.2: 47 percent / NaBH₄ / CH₂Cl₂; methanol / 2 h / 0 - 20 °C

4.1: DMAP / CH₂Cl₂ / 0.5 h

4.2: 95 percent / 1 h / 20 °C

5.1: 4A molecular sieves; di-tert-butylpyridine / CH₂Cl₂ / 0.5 h / 20 °C

5.2: 54 percent / MeOTf / 20 h / 0 °C

With dmap; 2,2'-dimethyldioxirane; 4 A molecular sieve; acetic anhydride; dimethyl sulfoxide; Di-tert-butylpyridine; trifluoroacetic anhydride; In dichloromethane; acetone;
DOI:10.1021/jo015521z