Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
CAS No.:187456-16-2
Molecular Formula:C₄₃H₄₈Cl₃NO₁₆
Molecular Weight:941.21
Hs Code.:

Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Synonyms:Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

There total 7 articles about Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl 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: 76.0%

: 136945-14-7
O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate

: 125884-36-8
methyl 6-O-benzoyl-2,3-di-O-benzyl-α-D-galactopyranoside

: 187456-16-2
Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 0.25h; Ambient temperature;
DOI:10.1016/S0008-6215(96)00237-6

Reference yield:

: 59042-16-9
(3R,4R,5S,6R)-6-(acetoxymethyl)-3-aminotetrahydro-2H-pyran-2,4,5-triyl triacetate

: 187456-16-2
Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / EtN(i-Pr)2

2: 83 percent / N₂H₄*HOAc / dimethylformamide / 0.33 h / Ambient temperature

3: 73 percent / DBU / CH₂Cl₂ / 0.33 h / Ambient temperature

4: 76 percent / TMSOTf / CH₂Cl₂ / 0.25 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(96)00237-6

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 187456-16-2
Benzoic acid (2R,3S,4S,5R,6S)-4,5-bis-benzyloxy-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: NaHCO₃ / H₂O / 1 h

2: pyridine / Ambient temperature

3: 83 percent / N₂H₄*HOAc / dimethylformamide / 0.33 h / Ambient temperature

4: 73 percent / DBU / CH₂Cl₂ / 0.33 h / Ambient temperature

5: 76 percent / TMSOTf / CH₂Cl₂ / 0.25 h / Ambient temperature

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(96)00237-6