(2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran
CAS No.:189758-76-7
Molecular Formula:C₂₁H₂₅BrO₄
Molecular Weight:421.331
Hs Code.:

Synonyms:(2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran

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Technology Process of (2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran

There total 4 articles about (2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran 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%

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 189758-74-5
(2S,3S,4R,6S)-2-Bromomethyl-6-methoxy-tetrahydro-pyran-3,4-diol

: 189758-76-7
(2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran

Guidance literature:: With trifluorormethanesulfonic acid; In cyclohexane; for 24h; Ambient temperature;
DOI:10.1002/chem.19970030318

Reference yield:

: 69617-72-7
(3S,4S,5R,1'S)-3-bromo-5-(2'-bromo-1'-hydroxy)ethyl-4,5-dihydro-4-hydroxy-2-(3H)-furanone

: 189758-76-7
(2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1: Amberlite IR 120 (H(+)), NaBH₄ / aq. ethanol

2: 48 percent / conc. H₂SO₄ / 46 h / Heating

3: 80 percent / H₂, Et₃N / 5percent Pd/C / ethanol / 19 h / 20 °C / 760 Torr

4: 76 percent / TfOH / cyclohexane / 24 h / Ambient temperature

With sodium tetrahydroborate; trifluorormethanesulfonic acid; Amberlite IR 120 (H(+)); sulfuric acid; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; cyclohexane;
DOI:10.1002/chem.19970030318

Reference yield:

: 122204-66-4
methyl 2,6-dibromo-2,6-dideoxy-α-D-mannopyranoside

: 189758-76-7
(2S,3S,4R,6S)-3,4-Bis-benzyloxy-2-bromomethyl-6-methoxy-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: 80 percent / H₂, Et₃N / 5percent Pd/C / ethanol / 19 h / 20 °C / 760 Torr

2: 76 percent / TfOH / cyclohexane / 24 h / Ambient temperature

With trifluorormethanesulfonic acid; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; cyclohexane;
DOI:10.1002/chem.19970030318