4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 219906-55-5
• Molecular Formula: C₄₅H₇₄O₁₂Si₃
• Molecular Weight: 891.332
• Mol file: 219906-55-5.mol

Synonyms:4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester

Chemical Property of 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester

There total 10 articles about 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-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:

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester (219906-55-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 31 percent / HCl gas / Ambient temperature

2: 65 percent / pyridine / -35 - 20 °C

3: 93 percent / imidazole, DMAP / dimethylformamide / 1 h

4: 76 percent / Et₃N, H₂ / Pd/C / ethyl acetate / 24 h / 50 °C / 760 Torr

5: 79 percent / DBU / CH₂Cl₂ / 3 h / Ambient temperature

6: 1.) BF₃*OEt₂, 4A MS, 2.) 2,6-lutidine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -20 deg C, 1 h

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; dmap; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo981685c

Reference yield:

benzyl 2-O-(4-methoxybenzoyl)-α-D-xylopyranoside (219906-49-7) → 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester (219906-55-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / imidazole, DMAP / dimethylformamide / 1 h

2: 76 percent / Et₃N, H₂ / Pd/C / ethyl acetate / 24 h / 50 °C / 760 Torr

3: 79 percent / DBU / CH₂Cl₂ / 3 h / Ambient temperature

4: 1.) BF₃*OEt₂, 4A MS, 2.) 2,6-lutidine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -20 deg C, 1 h

With 1H-imidazole; 2,6-dimethylpyridine; dmap; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo981685c

Reference yield:

4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-benzyloxy-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester (219906-50-0) → 4-Methoxy-benzoic acid (2S,3R,4R,5R)-2-((2S,3R,4R,5S)-3-acetoxy-2-benzyloxy-5-triethylsilanyloxy-tetrahydro-pyran-4-yloxy)-4,5-bis-triethylsilanyloxy-tetrahydro-pyran-3-yl ester (219906-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / Et₃N, H₂ / Pd/C / ethyl acetate / 24 h / 50 °C / 760 Torr

2: 79 percent / DBU / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.) BF₃*OEt₂, 4A MS, 2.) 2,6-lutidine / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, -20 deg C, 1 h

With 2,6-dimethylpyridine; boron trifluoride diethyl etherate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1021/jo981685c

upstream raw materials:

triethylsilyl trifluoromethyl sulfonate

benzyl 2-O-acetyl-β-L-arabinopyranoside

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-α,β-D-xylopyranosyl trichloroacetimidate

D-Xylose

Downstream raw materials:

C₇₃H₁₂₈O₁₆Si₄

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

3β,16β,17α-trihydroxycholest-5-en-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-β-L-arabinopyranoside}