Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester
CAS No.:115678-21-2
Molecular Formula:C₂₇H₂₇BrO₅
Molecular Weight:511.412
Hs Code.:

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

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

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

There total 6 articles about Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-bromo-6-methyl-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:

: 115678-20-1
methyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

: 115678-21-2
Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With bromine; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1021/jo00252a030

Reference yield:

: 100-39-0
benzyl bromide

: 115678-21-2
Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, 1 h, 2.) 10 deg C, 2 h

2: 86.4 percent / trifluoroacetic acid / methanol / 2 h / 50 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylamonium bromide / 1.) C₆H₆, reflux, 5 h, 2.) 50 deg C, 3 h

4: 89.8 percent / pyridine / 12 h / 0 °C

5: Br₂ / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; tetrabutylammomium bromide; bromine; sodium hydride; di(n-butyl)tin oxide; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/jo00252a030

Reference yield:

: 115678-10-9
methyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 115678-21-2
Benzoic acid (2S,3R,4R,5S,6S)-4,5-bis-benzyloxy-2-bromo-6-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, 1 h, 2.) 10 deg C, 2 h

2: 86.4 percent / trifluoroacetic acid / methanol / 2 h / 50 °C

3: 1.) dibutyltin oxide, 2.) tetrabutylamonium bromide / 1.) C₆H₆, reflux, 5 h, 2.) 50 deg C, 3 h

4: 89.8 percent / pyridine / 12 h / 0 °C

5: Br₂ / CH₂Cl₂ / 0.33 h / 0 °C

With pyridine; tetrabutylammomium bromide; bromine; sodium hydride; di(n-butyl)tin oxide; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/jo00252a030