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

Base Information

Chemical Name:Benzoic acid (2S,3R,4R,5R,6R)-6-acetoxymethyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester
CAS No.:211795-76-5
Molecular Formula:C₃₈H₅₆O₁₄SSi
Molecular Weight:797.006
Hs Code.:

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

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

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Technology Process of Benzoic acid (2S,3R,4R,5R,6R)-6-acetoxymethyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester

There total 19 articles about Benzoic acid (2S,3R,4R,5R,6R)-6-acetoxymethyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-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:

: 73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6
6-deoxy-L-galactose

: 211795-76-5
Benzoic acid (2S,3R,4R,5R,6R)-6-acetoxymethyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: p-TsOH, Amberlite IR 120 / 4 h / Heating

2: p-TsOH / 2 h

3: 91 percent / NaH / dimethylformamide / 0.5 h / Ambient temperature

4: 96 percent / AcOH, H₂O / 6 h / 40 °C

5: pyridine / 18 h / Ambient temperature

6: 75 percent / RhCl(PPh₃)3, DBU, H₂O / ethanol / 1 h / 90 °C

7: 95 percent / DBU / 0.5 h / Ambient temperature

8: 75 percent / TMSOTf / CH₂Cl₂ / 0.17 h / Ambient temperature

9: 88 percent / DDQ / CH₂Cl₂ / Ambient temperature

10: pyridine / 4 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; RhCl(PPh₃)3; Amberlite IR 120; water; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(97)10044-1

Reference yield:

: 98-88-4
benzoyl chloride

: 211795-76-5
Benzoic acid (2S,3R,4R,5R,6R)-6-acetoxymethyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 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

6: NaOMe / methanol / 0.33 h / Ambient temperature

7: 75 percent / TMSOTf / CH₂Cl₂ / 0.17 h / Ambient temperature

8: 88 percent / DDQ / CH₂Cl₂ / Ambient temperature

9: pyridine / 4 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; water; sodium methylate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(97)10044-1

Reference yield:

: 108182-34-9
allyl 3,4-di-O-isopropylidene-α-L-fucopyranoside

: 211795-76-5
Benzoic acid (2S,3R,4R,5R,6R)-6-acetoxymethyl-4-allyloxy-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-5-((2S,3S,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 91 percent / NaH / dimethylformamide / 0.5 h / Ambient temperature

2: 96 percent / AcOH, H₂O / 6 h / 40 °C

3: pyridine / 18 h / Ambient temperature

4: 75 percent / RhCl(PPh₃)3, DBU, H₂O / ethanol / 1 h / 90 °C

5: 95 percent / DBU / 0.5 h / Ambient temperature

6: 75 percent / TMSOTf / CH₂Cl₂ / 0.17 h / Ambient temperature

7: 88 percent / DDQ / CH₂Cl₂ / Ambient temperature

8: pyridine / 4 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; RhCl(PPh₃)3; water; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(97)10044-1