6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde

Base Information

• Chemical Name: 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde
• CAS No.: 163082-09-5
• Molecular Formula: C₂₉H₃₃NO₈
• Molecular Weight: 523.583

Synonyms:6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde

Chemical Property of 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde

There total 16 articles about 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde 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: 83.0%

benzyl bromide (100-39-0) + 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-hydroxy-1,3-benzodioxole-5-carbaldehyde (163082-08-4) → 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde (163082-09-5)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide;

DOI:10.1021/ja00117a046

Reference yield:

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene (67451-62-1,82683-92-9,132958-32-8,130792-45-9) → 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde (163082-09-5)

Guidance literature:

Multi-step reaction with 8 steps

1: p-TsOH*H₂O / acetone / 0.33 h / Ambient temperature

2: 54 percent / Cu(acac)2 / acetonitrile / 1 h / Ambient temperature

3: 78 percent / Bu₃SnH, AIBN / tetrahydrofuran / 2 h / Heating

4: 1.) s-BuLi, TMEDA, 2.) CuCN, 3.) BF₃*Et₂O

5: 1.) s-BuLi / 1.) hexane, THF, 0 deg C, 15 min, 2.) hexane, THF, reflux, 4 d

6: 20 percent / sodium anthracenide / 1,2-dimethoxy-ethane / 0.25 h / -78 °C

7: 72 percent / sodium bis(2-methoxyethoxy)aluminum hydride, morpholine / toluene; tetrahydrofuran / 31 h / -45 °C

8: 83 percent / K₂CO₃ / dimethylformamide / 4 h / Ambient temperature

With morpholine; copper acetylacetonate; sodium anthracenide; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sec.-butyllithium; tri-n-butyl-tin hydride; potassium carbonate; toluene-4-sulfonic acid; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1021/ja960596j

Reference yield:

(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole (130669-75-9) → 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carbaldehyde (163082-09-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 54 percent / Cu(acac)2 / acetonitrile / 1 h / Ambient temperature

2: 78 percent / Bu₃SnH, AIBN / tetrahydrofuran / 2 h / Heating

3: 1.) s-BuLi, TMEDA, 2.) CuCN, 3.) BF₃*Et₂O

4: 1.) s-BuLi / 1.) hexane, THF, 0 deg C, 15 min, 2.) hexane, THF, reflux, 4 d

5: 20 percent / sodium anthracenide / 1,2-dimethoxy-ethane / 0.25 h / -78 °C

6: 72 percent / sodium bis(2-methoxyethoxy)aluminum hydride, morpholine / toluene; tetrahydrofuran / 31 h / -45 °C

7: 83 percent / K₂CO₃ / dimethylformamide / 4 h / Ambient temperature

With morpholine; copper acetylacetonate; sodium anthracenide; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; boron trifluoride diethyl etherate; sec.-butyllithium; tri-n-butyl-tin hydride; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja960596j

upstream raw materials:

benzyl bromide

6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-hydroxy-1,3-benzodioxole-5-carbaldehyde

dimetilamide dell'acido 3,4-metilendiossibenzoico

cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene

Downstream raw materials:

(3'aS,4'R,5'R,7'aR)-7-Benzyloxy-4'-tert-butoxycarbonylamino-2',2'-dimethyl-3'a,4',5',7'a-tetrahydro-[5,5']bi[benzo[1,3]dioxolyl]-6-carboxylic acid

pancratistatin

methyl 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-(isopropylidenedioxy)-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carboxylate

methyl 6-<(1R,4R,5S,6R)-6-<(tert-butyloxycarbonyl)amino>-4,5-dihydroxy-2-cyclohexen-1-yl>-4-(phenylmethoxy)-1,3-benzodioxole-5-carboxylate

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