N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Base Information

Chemical Name:N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide
CAS No.:183051-72-1
Molecular Formula:C₄₄H₅₁NO₁₁
Molecular Weight:769.889
Hs Code.:

N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Synonyms:N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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Chemical Property of N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

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Technology Process of N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

There total 9 articles about N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 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:

: 70831-94-6
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

: 183051-72-1
N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Ag₂CO₃, AgClO₄, 4A molecular sieves, 2.) 4A molecular sieves / 1.) CH₂Cl₂, RT, 18 h, 2.) CH₂Cl₂, RT, 24 h

2: CH₃ONa, CH₃OH / 0.67 h / Ambient temperature

3: H₂N-NH₂*H₂O / ethanol; H₂O / 1 h / Heating

4: methanol / 0.5 h / Ambient temperature

5: 1.) drierite, 2.) (R)-(-)-camphor-10-sulfonic acid / 1.) CH₃CN, RT, 15 h, 2.) CH₃CN, RT, 5 h

With methanol; calcium sulfate; 4 A molecular sieve; (R)-10-camphorsulfonic acid; sodium methylate; silver perchlorate; hydrazine hydrate; silver carbonate; In methanol; ethanol; water;
DOI:10.1016/0968-0896(96)00105-8

Reference yield:

: 18997-88-1
1-O-ethyl-β-D-galactopyranoside

: 183051-72-1
N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) Bu₂SnO, 2.) tetrabutylammonium bromide, 4A molecular sieves / 1.) CH₃OH, 70 deg C, 6 h, 2.) benzene, 80 deg C, 1.5 h

2: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 1 h

3: 94 percent / aq. Ce(NH₄)2(NO₃)6 / acetonitrile / 2 h / Ambient temperature

4: 1.) Ag₂CO₃, AgClO₄, 4A molecular sieves, 2.) 4A molecular sieves / 1.) CH₂Cl₂, RT, 18 h, 2.) CH₂Cl₂, RT, 24 h

5: CH₃ONa, CH₃OH / 0.67 h / Ambient temperature

6: H₂N-NH₂*H₂O / ethanol; H₂O / 1 h / Heating

7: methanol / 0.5 h / Ambient temperature

8: 1.) drierite, 2.) (R)-(-)-camphor-10-sulfonic acid / 1.) CH₃CN, RT, 15 h, 2.) CH₃CN, RT, 5 h

With methanol; calcium sulfate; ammonium cerium(IV) nitrate; 4 A molecular sieve; (R)-10-camphorsulfonic acid; tetrabutylammomium bromide; sodium methylate; silver perchlorate; sodium hydride; di(n-butyl)tin oxide; hydrazine hydrate; silver carbonate; In methanol; ethanol; water; acetonitrile;
DOI:10.1016/0968-0896(96)00105-8

Reference yield:

: 183051-69-6
ethyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside

: 183051-72-1
N-[(2R,4aR,6S,7R,8R,8aS)-6-((2R,3S,4S,5R,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran-4-yloxy)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 1 h

2: 94 percent / aq. Ce(NH₄)2(NO₃)6 / acetonitrile / 2 h / Ambient temperature

3: 1.) Ag₂CO₃, AgClO₄, 4A molecular sieves, 2.) 4A molecular sieves / 1.) CH₂Cl₂, RT, 18 h, 2.) CH₂Cl₂, RT, 24 h

4: CH₃ONa, CH₃OH / 0.67 h / Ambient temperature

5: H₂N-NH₂*H₂O / ethanol; H₂O / 1 h / Heating

6: methanol / 0.5 h / Ambient temperature

7: 1.) drierite, 2.) (R)-(-)-camphor-10-sulfonic acid / 1.) CH₃CN, RT, 15 h, 2.) CH₃CN, RT, 5 h

With methanol; calcium sulfate; ammonium cerium(IV) nitrate; 4 A molecular sieve; (R)-10-camphorsulfonic acid; sodium methylate; silver perchlorate; sodium hydride; hydrazine hydrate; silver carbonate; In methanol; ethanol; water; acetonitrile;
DOI:10.1016/0968-0896(96)00105-8