2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide

Base Information

Chemical Name:2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide
CAS No.:122950-00-9
Molecular Formula:C₂₂H₃₀BrNO₅
Molecular Weight:468.388
Hs Code.:

Synonyms:2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide

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Chemical Property of 2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide

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Technology Process of 2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide

There total 7 articles about 2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-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: 94.0%

: methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-((N,N-dimethylcarbamoyl)methyl)-3-C-vinyl-α-D-allopyranoside

: 122950-00-9
2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide

Guidance literature:: With pyridine; N-Bromosuccinimide; triphenylphosphine; In dichloromethane; at 0 ℃;
DOI:10.1021/jo00283a033

Reference yield:

: 122672-65-5
methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribohexopyranosid-3-ulose

: 122950-00-9
2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / acetonitrile / 72 h / Heating

2: 71 percent / DIBAL / CH₂Cl₂

3: 68 percent / molecular sieves 4A / toluene / 10 h

4: 81 percent / imidazole / tetrahydrofuran / 1 h / Ambient temperature

5: 94 percent / Ph₃P, N-bromosuccinimide, pyridine / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; N-Bromosuccinimide; 4 A molecular sieve; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00283a033

Reference yield:

: 194149-26-3
methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

: 122950-00-9
2-[(2R,4aR,6S,7R,8S,8aS)-7-(2-Bromo-ethyl)-6-methoxy-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl]-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-BuLi, 2.) hexamethylphosphoramide / 1.) THF, from -40 deg C to -30 deg C, 30 min, 2.) THF, from -35 deg C to -30 deg C

2: 98 percent / acetonitrile / 72 h / Heating

3: 71 percent / DIBAL / CH₂Cl₂

4: 68 percent / molecular sieves 4A / toluene / 10 h

5: 81 percent / imidazole / tetrahydrofuran / 1 h / Ambient temperature

6: 94 percent / Ph₃P, N-bromosuccinimide, pyridine / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; n-butyllithium; 4 A molecular sieve; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo00283a033