Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

Base Information

Chemical Name:Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester
CAS No.:160054-03-5
Molecular Formula:C₃₀H₃₃NO₇
Molecular Weight:519.595
Hs Code.:

Synonyms:Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

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Chemical Property of Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

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Technology Process of Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

There total 12 articles about Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl 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:

: 160054-02-4
Acetic acid (1S,4S,5R,6R)-4-benzylcarbamoyloxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

: 160054-03-5
Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

Guidance literature:: With potassium carbonate; In methanol; Yield given;
DOI:10.1016/S0040-4039(00)77001-8

Reference yield:

: 137915-37-8
1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

: 160054-03-5
Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 74 percent / NaH

2: 1.) dimethyldioxirane / 1.) acetone/CH₂Cl₂, 2.) room temperature

3: DMAP, pyridine

4: 91 percent / TBAF / tetrahydrofuran; ethyl acetate

5: 93 percent / pyridine, DMAP

6: 94 percent / KI / dimethylformamide / 2 h / 100 °C

7: 97 percent / AgF, pyridine / 24 h / Ambient temperature

8: 1.) HgCl₂, 2.) MsCl, DMAP, pyridine / 1.) acetone/water, reflux, 4 h, 2.) room temperature, 5 h

9: 92 percent / NaBH₄, CeCl₃ / ethanol / 0.17 h / -78 °C

10: 98 percent / benzene / Heating

11: K₂CO₃ / methanol

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silver fluoride; sodium hydride; potassium carbonate; methanesulfonyl chloride; potassium iodide; mercury dichloride; In tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)77001-8

Reference yield:

: 137895-61-5
3,4-di-O-(4-methoxybenzyl)-6-O-(triisopropylsilyl)-D-glucal

: 160054-03-5
Benzyl-carbamic acid (1S,4S,5R,6R)-4-hydroxy-5,6-bis-(4-methoxy-benzyloxy)-cyclohex-2-enyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) dimethyldioxirane / 1.) acetone/CH₂Cl₂, 2.) room temperature

2: DMAP, pyridine

3: 91 percent / TBAF / tetrahydrofuran; ethyl acetate

4: 93 percent / pyridine, DMAP

5: 94 percent / KI / dimethylformamide / 2 h / 100 °C

6: 97 percent / AgF, pyridine / 24 h / Ambient temperature

7: 1.) HgCl₂, 2.) MsCl, DMAP, pyridine / 1.) acetone/water, reflux, 4 h, 2.) room temperature, 5 h

8: 92 percent / NaBH₄, CeCl₃ / ethanol / 0.17 h / -78 °C

9: 98 percent / benzene / Heating

10: K₂CO₃ / methanol

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; 3,3-dimethyldioxirane; silver fluoride; potassium carbonate; methanesulfonyl chloride; potassium iodide; mercury dichloride; In tetrahydrofuran; methanol; ethanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)77001-8