N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Base Information

Chemical Name:N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide
CAS No.:271248-81-8
Molecular Formula:C₃₉H₄₃NO₁₁
Molecular Weight:701.771
Hs Code.:

N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Synonyms:N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

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Chemical Property of N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

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Technology Process of N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

There total 9 articles about N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-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:

: 271248-80-7
Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-2-((4aR,6S,7R,8R,8aR)-7-acetylamino-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-3-yl ester

: 271248-81-8
N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: With water; triethylamine; In methanol; at 4 ℃;
DOI:10.1039/a908511d

Reference yield:

: 3554-91-4
Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside

: 271248-81-8
N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 2 steps

1: 73 percent / TESOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

2: H₂O; Et₃N / methanol / 4 °C

With 4 A molecular sieve; water; triethylsilyl trifluoromethyl sulfonate; triethylamine; In methanol; dichloromethane; 1: Etherification / 2: Deacetylation;
DOI:10.1039/a908511d

Reference yield:

: 939-26-4
2-bromomethylnaphthyl bromide

: 271248-81-8
N-{(4aR,6S,7R,8R,8aR)-6-Benzyloxy-2-phenyl-8-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(naphthalen-2-ylmethoxymethyl)-tetrahydro-pyran-2-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-acetamide

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / KOH; 18-crown-6 / tetrahydrofuran / 2 °C

2: 95 percent / AcOH; H₂O / 75 °C

3: pyridine; DMAP

4: hydrazine acetate / dimethylformamide / 2 h

5: 90 percent / DBU / CH₂Cl₂ / -10 °C

6: 73 percent / TESOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

7: H₂O; Et₃N / methanol / 4 °C

With pyridine; dmap; potassium hydroxide; 18-crown-6 ether; 4 A molecular sieve; water; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Hydrolysis / 3: Acetylation / 4: Deacetylation / 5: Addition / 6: Etherification / 7: Deacetylation;
DOI:10.1039/a908511d