Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

Base Information

Chemical Name:Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester
CAS No.:187479-03-4
Molecular Formula:C₃₉H₅₄N₂O₉
Molecular Weight:694.866
Hs Code.:

Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

Synonyms:Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

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Chemical Property of Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

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Technology Process of Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

There total 19 articles about Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-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: 82.0%

: 3173-56-6
benzyl isothiocyanate

: 187479-02-3
(2R,5S,8S,9R,13R,13aS)-9-Heptyl-2-hydroxy-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-octahydro-6,10-dioxa-3a-aza-cyclopentacyclododecene-4,7,11-trione

: 187479-03-4
Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

Guidance literature:: With dmap; In dichloromethane;
DOI:10.1021/jo962180u

Reference yield:

: 187479-10-3
(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(4-methoxy-benzyloxy)-but-3-enyl]-pyrrolidine-1-carboxylic acid benzyl ester

: 187479-03-4
Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 74 percent / O₃, PPh₃ / CH₂Cl₂ / 1.) -78 deg C, 15 min, 2.) 25 deg C, 15 h

2: 100 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 15 h / 25 °C

3: 75 percent / DMAP, EDC / CH₂Cl₂ / 15 h / 25 °C

4: 76 percent / O₃, PPh₃ / CH₂Cl₂ / 1.) -78 deg C, 15 min,2.) 25 deg C, 15 h

5: 100 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 15 h / 25 °C

6: 86 percent / DMAP, EDC / CH₂Cl₂ / 15 h / 25 °C

7: 1.) H₂, 2.) DIPEA, BOP-Cl / 1.) W-2 Raney Ni / 1.) EtOH, 1 atm, 25 deg C, 38 h, 2.) toluene, 85 deg C, 16 h

8: 85 percent / 70percent HF / pyridine; tetrahydrofuran / 15 h / 25 °C

9: 82 percent / DMAP / CH₂Cl₂ / 15 h / 25 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; W-2 Raney Ni; In tetrahydrofuran; pyridine; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo9708396

Reference yield:

: 187479-11-4
(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(4-methoxy-benzyloxy)-3-oxo-propyl]-pyrrolidine-1-carboxylic acid benzyl ester

: 187479-03-4
Benzyl-carbamic acid (2R,5S,8S,9R,13R,13aS)-9-heptyl-5-isopropyl-13-(4-methoxy-benzyloxy)-8-methyl-4,7,11-trioxo-decahydro-6,10-dioxa-3a-aza-cyclopentacyclododecen-2-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 15 h / 25 °C

2: 75 percent / DMAP, EDC / CH₂Cl₂ / 15 h / 25 °C

3: 76 percent / O₃, PPh₃ / CH₂Cl₂ / 1.) -78 deg C, 15 min,2.) 25 deg C, 15 h

4: 100 percent / 2-methyl-2-butene, NaClO₂, NaH₂PO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 15 h / 25 °C

5: 86 percent / DMAP, EDC / CH₂Cl₂ / 15 h / 25 °C

6: 1.) H₂, 2.) DIPEA, BOP-Cl / 1.) W-2 Raney Ni / 1.) EtOH, 1 atm, 25 deg C, 38 h, 2.) toluene, 85 deg C, 16 h

7: 85 percent / 70percent HF / pyridine; tetrahydrofuran / 15 h / 25 °C

8: 82 percent / DMAP / CH₂Cl₂ / 15 h / 25 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydrogen fluoride; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; W-2 Raney Ni; In tetrahydrofuran; pyridine; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo9708396