((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine

Base Information

• Chemical Name: ((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine
• CAS No.: 1185202-66-7
• Molecular Formula: C₂₃H₄₁NO₃Si
• Molecular Weight: 407.669

Synonyms:((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine

Chemical Property of ((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine

Chemical Property:

Purity/Quality:

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Technology Process of ((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine

There total 37 articles about ((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine 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: 63.0%

((2R,3S,5S,6S)-2-(azidomethyl)-6-(3-(benzyloxy)propyl)-5-methyltetrahydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane (1438887-99-0) → ((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine (1185202-66-7)

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 4h;

DOI:10.1016/j.tetlet.2013.01.134

Reference yield:

4-benzyloxybutanal (5470-84-8) → ((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine (1185202-66-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: titanium tetrachloride / dichloromethane / -15 °C

1.2: 0.5 h / -15 °C

1.3: 1 h / -15 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

3.1: sodium tetrahydroborate; methanol / 1 h

4.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 2.08 h / 0 - 20 °C

5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -45 - 30 °C

5.2: 5 h / -40 - 0 °C

6.1: boron trifluoride diethyl etherate; ethane-1,2-dithiol / dichloromethane / 0.5 h / -20 °C

7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / 4 h / 0 - 20 °C

8.1: diethyl (2R,3R)-tartrate; titanium(IV) isopropylate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

8.2: 8 h / -20 °C

9.1: pyridine; Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

10.2: 0.33 h / -78 °C

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C

12.1: sodium hydride / tetrahydrofuran; dimethyl sulfoxide / 2 h / 20 °C

13.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Inert atmosphere

14.1: ozone; dimethylsulfide / dichloromethane / 0.08 h

15.1: sodium tetrahydroborate; methanol / 1 h / 0 °C

16.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.08 h / 0 °C

16.2: 3 h / 20 °C

17.1: triphenylphosphine; water / tetrahydrofuran / 4 h / 0 °C

With pyridine; titanium(IV) isopropylate; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; dimethylsulfide; diethyl (2R,3R)-tartrate; carbon tetrabromide; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; titanium tetrachloride; sodium hydride; Dess-Martin periodane; ozone; ethane-1,2-dithiol; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 8.1: |Sharpless Asymmetric Epoxidation / 8.2: |Sharpless Asymmetric Epoxidation;

DOI:10.1016/j.tetlet.2013.01.134

Reference yield:

4-benzyloxy-butan-1-ol (4541-14-4) → ((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanamine (1185202-66-7)

Guidance literature:

Multi-step reaction with 18 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

1.2: 1.5 h / -78 - 20 °C

2.1: titanium tetrachloride / dichloromethane / -15 °C

2.2: 0.5 h / -15 °C

2.3: 1 h / -15 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

4.1: sodium tetrahydroborate; methanol / 1 h

5.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 2.08 h / 0 - 20 °C

6.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -45 - 30 °C

6.2: 5 h / -40 - 0 °C

7.1: boron trifluoride diethyl etherate; ethane-1,2-dithiol / dichloromethane / 0.5 h / -20 °C

8.1: sodium bis(2-methoxyethoxy)aluminium dihydride / 4 h / 0 - 20 °C

9.1: diethyl (2R,3R)-tartrate; titanium(IV) isopropylate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

9.2: 8 h / -20 °C

10.1: pyridine; Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

11.2: 0.33 h / -78 °C

12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 °C

13.1: sodium hydride / tetrahydrofuran; dimethyl sulfoxide / 2 h / 20 °C

14.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Inert atmosphere

15.1: ozone; dimethylsulfide / dichloromethane / 0.08 h

16.1: sodium tetrahydroborate; methanol / 1 h / 0 °C

17.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.08 h / 0 °C

17.2: 3 h / 20 °C

18.1: triphenylphosphine; water / tetrahydrofuran / 4 h / 0 °C

With pyridine; titanium(IV) isopropylate; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethylsulfide; diethyl (2R,3R)-tartrate; carbon tetrabromide; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; titanium tetrachloride; sodium hydride; Dess-Martin periodane; ozone; ethane-1,2-dithiol; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 9.1: |Sharpless Asymmetric Epoxidation / 9.2: |Sharpless Asymmetric Epoxidation;

DOI:10.1016/j.tetlet.2013.01.134

upstream raw materials:

2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)acetic acid

((4S,5S)-1-(benzyloxy)-5-methyl-9-(tetrahydro-2H-pyran-2-yloxy)non-7-yn-4-yloxy)(tert-butyl)dimethylsilane

(5S,6S,E)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-en-1-ol

((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

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