((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Base Information

• Chemical Name: ((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester
• CAS No.: 515816-21-4
• Molecular Formula: C₂₅H₃₂O₅
• Molecular Weight: 412.526
• Mol file: 515816-21-4.mol

Synonyms:((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Chemical Property of ((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

There total 20 articles about ((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl 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: 96.0%

(E)-3-((1R,2R,3S)-3-Benzyloxy-1-benzyloxymethyl-4-bromo-2-methyl-butoxy)-acrylic acid ethyl ester (515816-19-0) → ((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (515816-21-4)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; Heating;

DOI:10.1016/S0960-894X(02)00821-1

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → ((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (515816-21-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: n-Bu₂BOTf; Et₃N / CH₂Cl₂ / 0 °C

1.2: CH₂Cl₂ / -78 °C

1.3: aq. H₂O₂ / CH₂Cl₂; methanol / 0 °C

2.1: Me₃Al / tetrahydrofuran; hexane / 20 °C

2.2: tetrahydrofuran; CH₂Cl₂; hexane / 20 °C

3.1: Mg / tetrahydrofuran / Heating

3.2: tetrahydrofuran / 20 °C

4.1: Et₃B / tetrahydrofuran; methanol; hexane / -78 °C

4.2: NaBH₄ / tetrahydrofuran; methanol; hexane / -78 °C

5.1: CSA / CH₂Cl₂ / 20 °C

6.1: DIBAL / CH₂Cl₂; hexane / 20 °C

7.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 20 °C

7.2: NaIO₄ / acetone; H₂O / 20 °C

7.3: NaBH₄ / ethanol / 0 °C

8.1: imidazole / CH₂Cl₂ / 0 °C

9.1: NMO / acetonitrile / 20 °C

10.1: aq. HCl / methanol / 0 °C

11.1: pyridine; PPh₃; CBr₄ / CH₂Cl₂ / 20 °C

12.1: AIBN; n-Bu₃SnH / benzene / Heating

With pyridine; 1H-imidazole; hydrogenchloride; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); triethyl borane; carbon tetrabromide; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; magnesium; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1021/jo034930n

Reference yield:

<3(2R,3R),4R,5S>-3-<3-hydroxy-2-methyl-1-oxo-4-(phenylmethoxy)butyl>-4-methyl-5-phenyl-2-oxazolidinone (129986-19-2) → ((2S,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-methyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (515816-21-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: Me₃Al / tetrahydrofuran; hexane / 20 °C

1.2: tetrahydrofuran; CH₂Cl₂; hexane / 20 °C

2.1: Mg / tetrahydrofuran / Heating

2.2: tetrahydrofuran / 20 °C

3.1: Et₃B / tetrahydrofuran; methanol; hexane / -78 °C

3.2: NaBH₄ / tetrahydrofuran; methanol; hexane / -78 °C

4.1: CSA / CH₂Cl₂ / 20 °C

5.1: DIBAL / CH₂Cl₂; hexane / 20 °C

6.1: OsO₄; N-methylmorpholine N-oxide / acetone; H₂O / 20 °C

6.2: NaIO₄ / acetone; H₂O / 20 °C

6.3: NaBH₄ / ethanol / 0 °C

7.1: imidazole / CH₂Cl₂ / 0 °C

8.1: NMO / acetonitrile / 20 °C

9.1: aq. HCl / methanol / 0 °C

10.1: pyridine; PPh₃; CBr₄ / CH₂Cl₂ / 20 °C

11.1: AIBN; n-Bu₃SnH / benzene / Heating

With pyridine; 1H-imidazole; hydrogenchloride; osmium(VIII) oxide; N-methyl-2-indolinone; 2,2'-azobis(isobutyronitrile); triethyl borane; carbon tetrabromide; camphor-10-sulfonic acid; trimethylaluminum; tri-n-butyl-tin hydride; diisobutylaluminium hydride; magnesium; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetone; acetonitrile; benzene;

DOI:10.1021/jo034930n

upstream raw materials:

(E)-3-((1R,2R,3S)-3-Benzyloxy-1-benzyloxymethyl-4-bromo-2-methyl-butoxy)-acrylic acid ethyl ester

ethanol

benzyloxyacetoaldehyde

<2R,3R>-3-hydroxy-N-methoxy-N,2-dimethyl-4-(phenylmethoxy)butanamide