Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
CAS No.:79698-62-7
Molecular Formula:C₂₂H₂₅NO₆
Molecular Weight:399.444
Hs Code.:

Synonyms:Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 2 articles about Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-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:

: 79698-60-5
Imidazole-1-sulfonic acid (2R,4aR,6S,7R,8R,8aR)-7-benzyloxycarbonylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

: 79698-62-7
Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / Bu₄I / benzene / 4 h / Heating

2: 1.) NBS, BaCO₃, 2.) Bu₃SnH, AIBN / 1.) CCl₄, reflux, 2.) toluene, 80 - 90 deg C

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; barium carbonate; In benzene;
DOI:10.1021/ja00410a056

Reference yield:

: 79698-61-6,80734-77-6
((2R,4aR,6S,7S,8aR)-8-Iodo-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-carbamic acid benzyl ester

: 79698-62-7
Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; barium carbonate; Yield given. Multistep reaction; 1.) CCl₄, reflux, 2.) toluene, 80 - 90 deg C;
DOI:10.1021/ja00410a056

Reference yield:

: 79698-62-7
Benzoic acid (2R,3S,5R,6S)-5-benzyloxycarbonylamino-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

: 79698-66-1
(2S,4S,5R)-4-Benzyloxy-5-methyl-tetrahydro-furan-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: NaOMe / methanol

2: H₂ / Pd/C / ethyl acetate

3: 1.) N₂O₃, 2.) HCl / 1.) H₂O, 2.) reflux, 30 min

4: 83 percent / NaH / tetrahydrofuran

5: aq. AcOH / tetrahydrofuran

With hydrogenchloride; dinitrogen trioxide; hydrogen; sodium methylate; sodium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate;
DOI:10.1021/ja00410a056