Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester
• CAS No.: 198200-42-9
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.402
• Mol file: 198200-42-9.mol

Synonyms:Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

There total 4 articles about Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl 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: 89.0%

benzoyl chloride (98-88-4) + (2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol (198200-41-8) → Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester (198200-42-9)

Guidance literature:

With pyridine; 4 A molecular sieve; at -30 ℃; for 0.5h;

DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside (198200-37-2) → Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester (198200-42-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridine / 2 h / Ambient temperature

2: 74 percent / DBU / dimethylformamide / 2.5 h / 75 °C

3: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

4: 89 percent / 4 Angstroem molecular sieves, pyridine / 0.5 h / -30 °C

With pyridine; 4 A molecular sieve; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)00149-3

Reference yield:

Acetic acid (2S,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester (198200-40-7) → Benzoic acid (2S,3R,4S,5S)-4-benzyloxy-5-hydroxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester (198200-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / NaOMe / methanol / 1.5 h / Ambient temperature

2: 89 percent / 4 Angstroem molecular sieves, pyridine / 0.5 h / -30 °C

With pyridine; 4 A molecular sieve; sodium methylate; In methanol;

DOI:10.1016/S0008-6215(97)00149-3

upstream raw materials:

benzoyl chloride

(2S,3R,4S,5S)-4-Benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3,5-diol

methyl 3-O-benzyl-6-deoxy-6-iodo-α-D-glucopyranoside

Acetic acid (2S,3R,4S,5S)-5-acetoxy-4-benzyloxy-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

Downstream raw materials:

Benzoic acid (2S,3R,4R,5S)-4-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

Benzoic acid (2S,3R,4R,5S)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-2-methoxy-6-methylene-tetrahydro-pyran-3-yl ester

(2R,3S,4R,5R,6S)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,3S,4S,5R,6S)-5-Benzoyloxy-4-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester