Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 389085-56-7
• Molecular Formula: C₃₂H₃₆O₆
• Molecular Weight: 516.634
• Mol file: 389085-56-7.mol

Synonyms:Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester

There total 1 articles about Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 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:

acetic anhydride (108-24-7) + (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran (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) + allyl-trimethyl-silane (762-72-1) → Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (389085-56-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; Yield given; Multistep reaction; 1.) MeCN, 0 deg C, 20 h, 2.) room temperature, 30 min;

DOI:10.1016/S0968-0896(98)00242-9

Reference yield: 97.0%

Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (389085-56-7) → ((2R,3R,4R,5R)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl)-methanol (388593-48-4)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1016/S0968-0896(98)00242-9

Reference yield:

Acetic acid (2R,3R,4R,5R)-6-allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-ylmethyl ester (389085-56-7) → N-[(2R,3S,4R,5S,6R)-6-(2,2-Dihydroxy-ethyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-ylmethyl]-3-phenyl-propionamide

Guidance literature:

Multi-step reaction with 7 steps

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

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

3: 82 percent / PPh₃ / H₂O; benzene / 5 h / Heating

4: 96.7 percent / Et₃N, HOBT, EDC / CH₂Cl₂ / 1.) 0 deg C, 30 min; 2.) 0 deg C to room temperature, 6 h

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

6: NaIO₄ / tetrahydrofuran; H₂O / 1 h

7: H₂ / Pd/C / tetrahydrofuran; H₂O / 6 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; diphenylphosphoranyl azide; hydrogen; sodium methylate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1016/S0968-0896(98)00242-9

upstream raw materials:

acetic anhydride

(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

allyl-trimethyl-silane

Downstream raw materials:

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

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

(2R,3R,4R,5R,6R)-2-Allyl-6-azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran

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