2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide

Base Information

Chemical Name:2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide
CAS No.:79440-56-5
Molecular Formula:C₁₉H₂₉NO₅
Molecular Weight:351.443
Hs Code.:

Synonyms:2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide

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Chemical Property of 2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide

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Technology Process of 2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide

There total 7 articles about 2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-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:

: 100-39-0
benzyl bromide

: 79440-56-5
2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 65 percent / NaH / hexamethylphosphoric acid triamide / 3 h

2: tetrahydrofuran / 24 h

3: Jones reagent / -10 °C

4: tetrahydrofuran / 2 h / -78 °C

5: aluminum amalgam, aq. acetic acid / 2.5 h / 25 °C

6: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 30percent H₂O₂, aq. NaOH / 1.) THF, reflux, 1.5 h, 2.) 25 deg C, 2 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; aluminium amalgam; dihydrogen peroxide; sodium hydride; acetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.1021/ja00411a044

Reference yield:

: 62158-33-2,62210-98-4
(3aS,4S,6S,7aS)-4-Hydroxymethyl-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one

: 79440-56-5
2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 65 percent / NaH / hexamethylphosphoric acid triamide / 3 h

2: tetrahydrofuran / 24 h

3: Jones reagent / -10 °C

4: tetrahydrofuran / 2 h / -78 °C

5: aluminum amalgam, aq. acetic acid / 2.5 h / 25 °C

6: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 30percent H₂O₂, aq. NaOH / 1.) THF, reflux, 1.5 h, 2.) 25 deg C, 2 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; aluminium amalgam; dihydrogen peroxide; sodium hydride; acetic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.1021/ja00411a044

Reference yield:

: 62158-32-1,67180-00-1
(3aS,4S,6S,7aS)-4-Benzyloxymethyl-6-methoxy-tetrahydro-furo[3,2-c]pyran-2-one

: 79440-56-5
2-((3R,4R,6R)-2-Benzyloxymethyl-4-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-N,N-dimethyl-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 24 h

2: Jones reagent / -10 °C

3: tetrahydrofuran / 2 h / -78 °C

4: aluminum amalgam, aq. acetic acid / 2.5 h / 25 °C

5: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 30percent H₂O₂, aq. NaOH / 1.) THF, reflux, 1.5 h, 2.) 25 deg C, 2 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; aluminium amalgam; dihydrogen peroxide; acetic acid; In tetrahydrofuran;
DOI:10.1021/ja00411a044