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

Base Information

Chemical Name:Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester
CAS No.:676241-01-3
Molecular Formula:C₃₁H₃₄O₆
Molecular Weight:502.607
Hs Code.:

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

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

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

There total 1 articles about Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-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: 80.0%

: 108-24-7
acetic anhydride

: 112219-66-6
(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-vinyltetrahydro-2H-pyran

: 676241-01-3
Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 1h;
DOI:10.1016/j.tetlet.2003.12.032

Reference yield: 66.0%

: 676241-01-3
Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

: 676241-03-5
((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 20h;
DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

: 676241-01-3
Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

: 676241-20-6
(2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium methylate / methanol / 20 h / 20 °C

2.1: triethylamine / dichloromethane / 20 h / 20 °C

3.1: sodium azide / N,N-dimethyl-formamide / 20 h / 90 °C

4.1: ozone / dichloromethane / 0.5 h / -78 °C

4.2: NaBH₄ / 11; 15 / 20 h / 20 °C

5.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide / acetone / 1 h / 20 °C

6.1: diethylphosphoryl cyanide; triethylamine / N,N-dimethyl-formamide / 72 h / 20 °C

7.1: water; triphenylphosphine / tetrahydrofuran / 20 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium azide; diethylphosphoryl cyanide; water; sodium methylate; ozone; triethylamine; triphenylphosphine; potassium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 1.1: Zemplen deacetylation / 7.1: Staundinger reaction;
DOI:10.1016/j.tetlet.2003.12.032