N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

Base Information

Chemical Name:N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide
CAS No.:223123-00-0
Molecular Formula:C₃₁H₃₅NO₆
Molecular Weight:517.622
Hs Code.:

Synonyms:N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

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Chemical Property of N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

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Technology Process of N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

There total 6 articles about N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-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: 86.0%

: N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2,3-dihydroxy-propyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

: 223123-00-0
N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; for 1h;
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

: 223123-00-0
N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

Guidance literature:: Multi-step reaction with 7 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: 91 percent / CH₂Cl₂ / 2 h / Ambient temperature

6: N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / Ambient temperature

7: 86 percent / NaIO₄ / tetrahydrofuran; H₂O / 1 h

With sodium periodate; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; diphenylphosphoranyl azide; sodium methylate; 4-methylmorpholine N-oxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; 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

: 223123-00-0
N-[(2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-(2-oxo-ethyl)-tetrahydro-pyran-2-ylmethyl]-acetamide

Guidance literature:: Multi-step reaction with 5 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: 91 percent / CH₂Cl₂ / 2 h / Ambient temperature

4: N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / Ambient temperature

5: 86 percent / NaIO₄ / tetrahydrofuran; H₂O / 1 h

With sodium periodate; osmium(VIII) oxide; diphenylphosphoranyl azide; 4-methylmorpholine N-oxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; acetone; tert-butyl alcohol; benzene;
DOI:10.1016/S0968-0896(98)00242-9