N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide

Base Information

Chemical Name:N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide
CAS No.:223122-85-8
Molecular Formula:C₃₉H₄₃NO₅
Molecular Weight:605.774
Hs Code.:

Synonyms:N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide

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Chemical Property of N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide

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Technology Process of N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide

There total 5 articles about N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide 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: 96.7%

: 223122-66-5
C-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methylamine

: 501-52-0
3-Phenylpropionic acid

: 223122-85-8
N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; 1.) 0 deg C, 30 min; 2.) 0 deg C to room temperature, 6 h;
DOI:10.1016/S0968-0896(98)00242-9

Reference yield:

: 3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9
(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

: 223122-85-8
N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) trimethylsilyl triflate / 1.) MeCN, 0 deg C, 20 h, 2.) room temperature, 30 min

2: 97 percent / NaOMe / methanol / 1 h / Ambient temperature

3: 87.6 percent / DEAD, PPh₃, diphenylphosphoryl azide / tetrahydrofuran / 1.) 0 deg C, 20 min; 2.) room temperature, overnight

4: 82 percent / PPh₃ / H₂O; benzene / 5 h / Heating

5: 96.7 percent / Et₃N, HOBT, EDC / CH₂Cl₂ / 1.) 0 deg C, 30 min; 2.) 0 deg C to room temperature, 6 h

With trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; sodium methylate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; benzene;
DOI:10.1016/S0968-0896(98)00242-9

Reference yield:

: 388593-48-4
((2R,3R,4R,5R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol

: 223122-85-8
N-((2R,3R,4R,5R,6R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl)-3-phenyl-propionamide

Guidance literature:: Multi-step reaction with 3 steps

1: 87.6 percent / DEAD, PPh₃, diphenylphosphoryl azide / tetrahydrofuran / 1.) 0 deg C, 20 min; 2.) room temperature, overnight

2: 82 percent / PPh₃ / H₂O; benzene / 5 h / Heating

3: 96.7 percent / Et₃N, HOBT, EDC / CH₂Cl₂ / 1.) 0 deg C, 30 min; 2.) 0 deg C to room temperature, 6 h

With diphenylphosphoranyl azide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1016/S0968-0896(98)00242-9