(S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid

Base Information

• Chemical Name: (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid
• CAS No.: 175085-05-9
• Molecular Formula: C₁₈H₂₂O₆
• Molecular Weight: 334.369
• Mol file: 175085-05-9.mol

Synonyms:(S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid

Chemical Property of (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid

There total 14 articles about (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid 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: 98.0%

(S)-2-methoxy-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate (175085-04-8) → (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid (175085-05-9)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium n-propylmercaptide; Inert atmosphere;

DOI:10.1021/ja207331m

Reference yield: 83.0%

Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester (855282-15-4) → (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid (175085-05-9)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/ja050728l

Reference yield:

(R)-1-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)ethane-1,2-diol (855282-45-0) → (S)-2-(benzoyloxy)-2-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)acetic acid (175085-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / DIPEA / tetrahydrofuran

2: 94 percent / DMAP; DIPEA / tetrahydrofuran

3: 83 percent / PDC / dimethylformamide / 12 h / 20 °C

With dmap; dipyridinium dichromate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja050728l

upstream raw materials:

(S)-2-methoxy-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate

Benzoic acid (R)-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethyl ester

(R)-1-((2R,5R,6R)-tetrahydro-2-methoxy-5,6-dimethyl-4-methylene-2H-pyran-2-yl)ethane-1,2-diol

(R)-1-((2R,5R,6R)-2-Methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-2-triethylsilanyloxy-ethanol

Downstream raw materials:

(S)-2-chloro-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate

(S)-2-methoxy-1-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl)-2-oxoethyl benzoate

Benzoic acid (S)-[(4R,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid (S)-[(4S,4aS,6R,8S,8aR)-6-((S)-2,3-diacetoxy-propyl)-8-methoxy-7,7-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylcarbamoyl]-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester