(2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:219865-42-6
Molecular Formula:C₂₈H₂₇BrO₈
Molecular Weight:571.422
Hs Code.:

Synonyms:(2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 8 articles about (2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-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: 54.0%

: 219864-92-3
(1S,3R,4R,5R,6S)-5-Benzoyloxy-3,4-bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]heptane-1-carboxylic acid methyl ester

: 219865-42-6
(2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: With titanium(IV) bromide; In dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo981477k

Reference yield:

: 219864-84-3
(2R,3S,4S,5R,6R)-5,6-Bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol

: 219865-42-6
(2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: NaHCO₃, KBr, TEMPO, NaOCl / tetrahydrofuran / 0.33 h / 0 °C

2: IR-120(H⁺) / 12 h / Ambient temperature

3: pyridine / 5 h / Ambient temperature

4: DBU / CH₂Cl₂ / 15 h / Ambient temperature

5: 64 percent / NBS / tetrahydrofuran; H₂O / Ambient temperature

6: 85 percent / Ag₂O / dimethylformamide; tetrahydrofuran / 15 h / Ambient temperature

7: 54 percent / TiBr₄ / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; N-Bromosuccinimide; IR-120(H⁺); titanium(IV) bromide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium bromide; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo981477k

Reference yield:

: (2S,3S,4S,5R,6R)-5,6-Bis-benzyloxy-3,4-dihydroxy-tetrahydro-pyran-2-carboxylic acid

: 219865-42-6
(2R,3S,4S,5R,6R)-4-Benzoyloxy-5,6-bis-benzyloxy-2-bromo-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: IR-120(H⁺) / 12 h / Ambient temperature

2: pyridine / 5 h / Ambient temperature

3: DBU / CH₂Cl₂ / 15 h / Ambient temperature

4: 64 percent / NBS / tetrahydrofuran; H₂O / Ambient temperature

5: 85 percent / Ag₂O / dimethylformamide; tetrahydrofuran / 15 h / Ambient temperature

6: 54 percent / TiBr₄ / CH₂Cl₂ / 0.5 h / -78 °C

With pyridine; N-Bromosuccinimide; IR-120(H⁺); titanium(IV) bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver(l) oxide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo981477k