Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 211795-72-1
• Molecular Formula: C₃₄H₄₈O₈SSi
• Molecular Weight: 644.902

Synonyms:

Chemical Property of Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-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,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 7 articles about Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-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:

benzoyl chloride (98-88-4) → Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (211795-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / pyridine / 18 h / Ambient temperature

2: 93 percent / TFA, H₂O / CH₂Cl₂ / Ambient temperature

3: 1) Bu₂SnO₂, 2) Bu₄NI / 1) toluene, reflux, 4 h, 2) toluene, 100 deg C, 22 h

4: pyridine / CH₂Cl₂ / 0 deg C, 1 h; 30 min, RT

5: dimethylformamide / 1 h / Ambient temperature

With pyridine; water; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10044-1

Reference yield:

(2S,4aR,6S,7R,8R,8aR)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (175980-93-5) → Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (211795-72-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) Bu₂SnO₂, 2) Bu₄NBr / 1) toluene, reflux, 18 h, 2) toluene, 60 deg C, 18 h

2: 89 percent / pyridine / 18 h / Ambient temperature

3: 93 percent / TFA, H₂O / CH₂Cl₂ / Ambient temperature

4: 1) Bu₂SnO₂, 2) Bu₄NI / 1) toluene, reflux, 4 h, 2) toluene, 100 deg C, 22 h

5: pyridine / CH₂Cl₂ / 0 deg C, 1 h; 30 min, RT

6: dimethylformamide / 1 h / Ambient temperature

With pyridine; tetrabutylammomium bromide; water; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10044-1

Reference yield:

Benzoic acid (2S,3R,4S,5S,6R)-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester (193221-61-3) → Benzoic acid (2S,3R,4R,5R,6R)-5-acetylsulfanyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester (211795-72-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) Bu₂SnO₂, 2) Bu₄NI / 1) toluene, reflux, 4 h, 2) toluene, 100 deg C, 22 h

2: pyridine / CH₂Cl₂ / 0 deg C, 1 h; 30 min, RT

3: dimethylformamide / 1 h / Ambient temperature

With pyridine; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(97)10044-1

upstream raw materials:

potassium thioacetate

benzoyl chloride

(2S,4aR,6S,7R,8R,8aR)-6-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Benzoic acid (2S,3R,4S,5S,6R)-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl ester

Downstream raw materials:

C₄₃H₅₂Cl₃NO₂₃S

C₄₉H₇₀O₂₃SSi

heptyl (2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1-4)-S-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-3)]-6-O-acetyl-2-O-benzoyl-1,4-dithio-β-D-glucopyranoside

Benzoic acid (2S,3R,4R,5R,6R)-4-allyloxy-5-[(2S,3S,4R,5R,6S)-4,5-diacetoxy-3-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran-2-ylsulfanyl]-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-3-yl ester

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