(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:180274-60-6
Molecular Formula:C₃₇H₃₉Cl₃N₄O₁₆
Molecular Weight:902.093
Hs Code.:

(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 10 articles about (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl 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: 84.0%

: 545-06-2
trichloroacetonitrile

: 180274-59-3
(2S,3S,4S,5R,6S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-6-hydroxy-4,5-bis-(4-methyl-benzoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 180274-60-6
(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; 1.) 0 deg C to r.t., 2.) r.t., 1 h;

Reference yield:

: 3150-20-7,6032-32-2,28541-75-5,85481-53-4,89731-58-8,109121-56-4,121468-39-1,12167-34-9
4-methoxyphenyl β-D-glucopyranoside

: 180274-60-6
(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 73 percent / p-TSA / 1 h / Ambient temperature

2: pyridine

3: MeOH, camphorsulfonic acid / Ambient temperature

4: 99 percent / imidazole / dimethylformamide

5: 42 percent / AgOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 1.) r.t., 40 min, 2.) 0 deg C, 1.5 h; r.t., 1 day

6: 89 percent / TBAF, AcOH / tetrahydrofuran / 120 h / Ambient temperature

7: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) 35 min

8: aq. NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol

9: ethyl acetate; diethyl ether

10: 88 percent / aq. CAN / acetonitrile / 2 h / 0 °C

11: 84 percent / DBU / CH₂Cl₂ / 1.) 0 deg C to r.t., 2.) r.t., 1 h

With pyridine; 1H-imidazole; methanol; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

Reference yield:

: 67817-15-6
Acetic acid (2R,3S,4R,5R,6R)-4-acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-3-yl ester

: 180274-60-6
(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-azido-tetrahydro-pyran-2-yloxy)-4,5-bis-(4-methyl-benzoyloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 42 percent / AgOTf, molecular sieves 4 Angstroem / CH₂Cl₂ / 1.) r.t., 40 min, 2.) 0 deg C, 1.5 h; r.t., 1 day

2: 89 percent / TBAF, AcOH / tetrahydrofuran / 120 h / Ambient temperature

3: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) 35 min

4: aq. NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol

5: ethyl acetate; diethyl ether

6: 88 percent / aq. CAN / acetonitrile / 2 h / 0 °C

7: 84 percent / DBU / CH₂Cl₂ / 1.) 0 deg C to r.t., 2.) r.t., 1 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; ammonium cerium(IV) nitrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetonitrile; tert-butyl alcohol;