[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Base Information

• Chemical Name: [(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester
• CAS No.: 215120-31-3
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 215120-31-3.mol

Synonyms:[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Chemical Property of [(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester

There total 3 articles about [(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl 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: 92.0%

[(2S,3R,4S,6S)-4-Benzyloxy-6-((E)-2-methoxy-vinyl)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester (225656-55-3) → [(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (215120-31-3)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 4.5h;

DOI:10.1021/ja982431b

Reference yield:

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (162718-31-2) → [(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (215120-31-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

2: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

3: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja982431b

Reference yield:

((2S,3R,4S,6S)-4-Benzyloxy-6-formyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester → [(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (215120-31-3)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

2: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

With trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja982431b

upstream raw materials:

[(2S,3R,4S,6S)-4-Benzyloxy-6-((E)-2-methoxy-vinyl)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester

Downstream raw materials:

[(2S,3R,4S,6S)-4-Benzyloxy-6-(2,2-bis-ethylsulfanyl-ethyl)-3-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

(2R,3S,4R,6R)-2-[(2S,4S,5R,6S)-4-Benzyloxy-6-(2-hydroxy-ethyl)-5-methyl-tetrahydro-pyran-2-ylmethyl]-2-methoxy-6-[(R)-2-(4-methoxy-benzyloxy)-1,1-dimethyl-but-3-enyl]-4-methyl-tetrahydro-pyran-3-ol

(1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

(4R,6R,8R)-1-{(2S,4S,5R,6S)-4-Benzyloxy-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-pyran-2-yl}-6-(tert-butyl-dimethyl-silanyloxy)-2-ethanesulfinyl-2-ethylsulfanyl-8-(4-methoxy-benzyloxy)-4,7,7-trimethyl-dec-9-en-3-ol