C₄₂H₅₁N₃O₁₈

Base Information

• Chemical Name: C₄₂H₅₁N₃O₁₈
• CAS No.: 588694-14-8
• Molecular Formula: C₄₂H₅₁N₃O₁₈
• Molecular Weight: 885.876
• Mol file: 588694-14-8.mol

Synonyms:C₄₂H₅₁N₃O₁₈

Chemical Property of C₄₂H₅₁N₃O₁₈

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₄₂H₅₁N₃O₁₈

There total 35 articles about C₄₂H₅₁N₃O₁₈ 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:

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetaldehyde (588693-73-6) → C42H51N3O18 (588694-14-8)

Guidance literature:

Multi-step reaction with 27 steps

1.1: 2-methyl-2-butene; aq. NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol / 1 h / 20 °C

2.1: 1.60 g / benzene; methanol / 1 h / 20 °C

3.1: CH₂Cl₂ / 0.25 h / 0 °C

4.1: 1.68 g / K₂CO₃ / methanol / 10 h / 0 °C

5.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C

6.1: LiBH₄ / tetrahydrofuran / 3 h / 20 °C

7.1: pyridine / 10 h / 50 °C

8.1: 2.15 g / Et₃N; DMAP / tetrahydrofuran / 48 h / 20 °C

9.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C

10.1: 98 percent / Na₂HPO₄; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C

11.1: 95 percent / Et₃N / CH₂Cl₂ / 0.67 h / -42 °C

12.1: Ac₂O; DMSO / 2 h / 20 °C

13.1: 1.04 g / NaBH₄ / methanol / 0.25 h / 0 °C

14.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C

15.1: 89 percent / TFA / methanol / 3 h / 20 °C

16.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

17.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C

18.1: NMO; OsO₄ / acetone; H₂O / 3 h / 20 °C

19.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C

20.1: NaBH₄ / methanol / 0.25 h / -78 °C

21.1: Et₃N; MeOH / 28.8 h / 15 °C

22.1: pyridine; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

22.2: pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

23.1: Pd(OH)2/C / methanol / 12 h / 20 °C

24.1: 96 mg / DMAP / pyridine / 2 h / 20 °C

25.1: 75 percent / aq. TFA / methanol; H₂O / 26.4 h / 20 °C

26.1: CAN / acetonitrile; H₂O / 2 h / 85 °C

27.1: 38.5 mg / Et₃N; HgCl₂ / dimethylformamide / 2 h / 20 °C

With pyridine; methanol; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; potassium tert-butylate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; tert-butyl alcohol; benzene; 12.1: Albright-Goldman reaction;

DOI:10.1021/ja0342998

Reference yield:

(1S,4R,6R)-4-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enol (588693-71-4) → C42H51N3O18 (588694-14-8)

Guidance literature:

Multi-step reaction with 28 steps

1.1: 94 percent / K₂CO₃; Bu₄NCl; NCS / TEMPO / CH₂Cl₂; aq. NaHCO₃ / 0.5 h / 20 °C

2.1: 2-methyl-2-butene; aq. NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol / 1 h / 20 °C

3.1: 1.60 g / benzene; methanol / 1 h / 20 °C

4.1: CH₂Cl₂ / 0.25 h / 0 °C

5.1: 1.68 g / K₂CO₃ / methanol / 10 h / 0 °C

6.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C

7.1: LiBH₄ / tetrahydrofuran / 3 h / 20 °C

8.1: pyridine / 10 h / 50 °C

9.1: 2.15 g / Et₃N; DMAP / tetrahydrofuran / 48 h / 20 °C

10.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C

11.1: 98 percent / Na₂HPO₄; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C

12.1: 95 percent / Et₃N / CH₂Cl₂ / 0.67 h / -42 °C

13.1: Ac₂O; DMSO / 2 h / 20 °C

14.1: 1.04 g / NaBH₄ / methanol / 0.25 h / 0 °C

15.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C

16.1: 89 percent / TFA / methanol / 3 h / 20 °C

17.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

18.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C

19.1: NMO; OsO₄ / acetone; H₂O / 3 h / 20 °C

20.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C

21.1: NaBH₄ / methanol / 0.25 h / -78 °C

22.1: Et₃N; MeOH / 28.8 h / 15 °C

23.1: pyridine; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

23.2: pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

24.1: Pd(OH)2/C / methanol / 12 h / 20 °C

25.1: 96 mg / DMAP / pyridine / 2 h / 20 °C

26.1: 75 percent / aq. TFA / methanol; H₂O / 26.4 h / 20 °C

27.1: CAN / acetonitrile; H₂O / 2 h / 85 °C

28.1: 38.5 mg / Et₃N; HgCl₂ / dimethylformamide / 2 h / 20 °C

With pyridine; methanol; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-chloro-succinimide; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; ammonium cerium(IV) nitrate; potassium tert-butylate; tetrabutyl-ammonium chloride; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 2,2,6,6-tetramethyl-piperidine-N-oxyl; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; sodium hydrogencarbonate; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; tert-butyl alcohol; benzene; 13.1: Albright-Goldman reaction;

DOI:10.1021/ja0342998

Reference yield:

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetic acid methyl ester (588693-75-8) → C42H51N3O18 (588694-14-8)

Guidance literature:

Multi-step reaction with 25 steps

1.1: CH₂Cl₂ / 0.25 h / 0 °C

2.1: 1.68 g / K₂CO₃ / methanol / 10 h / 0 °C

3.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C

4.1: LiBH₄ / tetrahydrofuran / 3 h / 20 °C

5.1: pyridine / 10 h / 50 °C

6.1: 2.15 g / Et₃N; DMAP / tetrahydrofuran / 48 h / 20 °C

7.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C

8.1: 98 percent / Na₂HPO₄; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C

9.1: 95 percent / Et₃N / CH₂Cl₂ / 0.67 h / -42 °C

10.1: Ac₂O; DMSO / 2 h / 20 °C

11.1: 1.04 g / NaBH₄ / methanol / 0.25 h / 0 °C

12.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C

13.1: 89 percent / TFA / methanol / 3 h / 20 °C

14.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

15.1: DBU / 1,2-dichloro-benzene / 0.33 h / 130 °C

16.1: NMO; OsO₄ / acetone; H₂O / 3 h / 20 °C

17.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C

18.1: NaBH₄ / methanol / 0.25 h / -78 °C

19.1: Et₃N; MeOH / 28.8 h / 15 °C

20.1: pyridine; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

20.2: pyridine; DMAP / CH₂Cl₂ / 2 h / 20 °C

21.1: Pd(OH)2/C / methanol / 12 h / 20 °C

22.1: 96 mg / DMAP / pyridine / 2 h / 20 °C

23.1: 75 percent / aq. TFA / methanol; H₂O / 26.4 h / 20 °C

24.1: CAN / acetonitrile; H₂O / 2 h / 85 °C

25.1: 38.5 mg / Et₃N; HgCl₂ / dimethylformamide / 2 h / 20 °C

With pyridine; methanol; dmap; lithium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; potassium tert-butylate; acetic anhydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; acetonitrile; 10.1: Albright-Goldman reaction;

DOI:10.1021/ja0342998

upstream raw materials:

N,N'-bis-Boc-S-methyl-isothiourea

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetaldehyde

(1S,4R,6R)-4-Benzyloxymethoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-hydroxy-eth-(E)-ylidene]-cyclohex-2-enol

[(2R,5S,6R)-2-Benzyloxymethoxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-cyclohex-3-en-(E)-ylidene]-acetic acid methyl ester

Downstream raw materials:

tetradotoxin

C₃₈H₃₉N₃O₁₆