Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester
• CAS No.: 588693-87-2
• Molecular Formula: C₅₄H₆₁NO₁₂
• Molecular Weight: 916.078
• Mol file: 588693-87-2.mol

Synonyms:Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester

Chemical Property of Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester

There total 20 articles about Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl 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:

Benzyloxymethyl chloride (3587-60-8) → Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester (588693-87-2)

Guidance literature:

Multi-step reaction with 20 steps

1.1: i-Pr₂NEt; DMAP / 1,2-dichloro-ethane / 4 h / 60 °C

2.1: (+/-)-CSA; MeOH / 1 h / 20 °C

3.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C

4.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C

5.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C

6.1: NaBH₄ / methanol / 0.25 h / 20 °C

7.1: (+/-)-CSA / acetone / 0.67 h / 20 °C

7.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C

8.1: 99 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

9.1: 94 percent / K₂CO₃; Bu₄NCl; NCS / TEMPO / CH₂Cl₂; aq. NaHCO₃ / 0.5 h / 20 °C

10.1: 2-methyl-2-butene; aq. NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol / 1 h / 20 °C

11.1: 1.60 g / benzene; methanol / 1 h / 20 °C

12.1: CH₂Cl₂ / 0.25 h / 0 °C

13.1: 1.68 g / K₂CO₃ / methanol / 10 h / 0 °C

14.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C

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

16.1: pyridine / 10 h / 50 °C

17.1: 2.15 g / Et₃N; DMAP / tetrahydrofuran / 48 h / 20 °C

18.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C

19.1: 98 percent / Na₂HPO₄; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C

20.1: 95 percent / Et₃N / CH₂Cl₂ / 0.67 h / -42 °C

With pyridine; methanol; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-chloro-succinimide; lithium borohydride; 2-methyl-but-2-ene; 10-camphorsufonic acid; potassium tert-butylate; tetrabutyl-ammonium chloride; magnesium ethylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; mercury(II) oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; pyridine; methanol; dichloromethane; sodium hydrogencarbonate; ethyl acetate; 1,2-dichloro-ethane; acetone; tert-butyl alcohol; benzene;

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) → Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester (588693-87-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 94 percent / K₂CO₃; Bu₄NCl; NCS / TEMPO / CH₂Cl₂; aq. NaHCO₃ / 0.5 h / 20 °C

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

3: 1.60 g / benzene; methanol / 1 h / 20 °C

4: CH₂Cl₂ / 0.25 h / 0 °C

5: 1.68 g / K₂CO₃ / methanol / 10 h / 0 °C

6: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C

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

8: pyridine / 10 h / 50 °C

9: 2.15 g / Et₃N; DMAP / tetrahydrofuran / 48 h / 20 °C

10: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C

11: 98 percent / Na₂HPO₄; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C

12: 95 percent / Et₃N / CH₂Cl₂ / 0.67 h / -42 °C

With pyridine; dmap; lithium hydroxide; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-chloro-succinimide; lithium borohydride; 2-methyl-but-2-ene; potassium tert-butylate; tetrabutyl-ammonium chloride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; methanol; dichloromethane; sodium hydrogencarbonate; 1,2-dichloro-ethane; tert-butyl alcohol; benzene;

DOI:10.1021/ja0342998

Reference yield:

Benzoic acid (1S,5R,8S,8aR)-5-benzyloxymethoxy-7-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxymethyl-3-methoxy-3,5,8,8a-tetrahydro-1H-isochromen-8-yl ester → Benzoic acid (1S,2S,3R,4R,5S,6R)-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester (588693-87-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 12.80 g / DMAP / pyridine / 3 h / 20 °C

2.1: 1.60 g / aq. PPTS; HgO / acetone / 7 h / 55 °C

3.1: Mg(OEt)2 / methanol; ethyl acetate / 1 h / 20 °C

4.1: NaBH₄ / methanol / 0.25 h / 20 °C

5.1: (+/-)-CSA / acetone / 0.67 h / 20 °C

5.2: 6.88 g / PPTS; MeOH / 0.08 h / 20 °C

6.1: 99 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

7.1: 94 percent / K₂CO₃; Bu₄NCl; NCS / TEMPO / CH₂Cl₂; aq. NaHCO₃ / 0.5 h / 20 °C

8.1: 2-methyl-2-butene; aq. NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol / 1 h / 20 °C

9.1: 1.60 g / benzene; methanol / 1 h / 20 °C

10.1: CH₂Cl₂ / 0.25 h / 0 °C

11.1: 1.68 g / K₂CO₃ / methanol / 10 h / 0 °C

12.1: 90 percent / t-BuOK / tetrahydrofuran / 0.5 h / -78 - -15 °C

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

14.1: pyridine / 10 h / 50 °C

15.1: 2.15 g / Et₃N; DMAP / tetrahydrofuran / 48 h / 20 °C

16.1: 85 percent / aq. LiOH / methanol; 1,2-dichloro-ethane / 24 h / 40 °C

17.1: 98 percent / Na₂HPO₄; m-CPBA / 1,2-dichloro-ethane / 12 h / 20 °C

18.1: 95 percent / Et₃N / CH₂Cl₂ / 0.67 h / -42 °C

With pyridine; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-chloro-succinimide; lithium borohydride; 2-methyl-but-2-ene; 10-camphorsufonic acid; potassium tert-butylate; tetrabutyl-ammonium chloride; magnesium ethylate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; mercury(II) oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; pyridine; methanol; dichloromethane; sodium hydrogencarbonate; ethyl acetate; 1,2-dichloro-ethane; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/ja0342998

upstream raw materials:

Benzyloxymethyl chloride

[(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

Benzoic acid (1S,2R,3S,4R,5S,6R)-2-acetoxy-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(2-oxo-ethyl)-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester

Benzoic acid (1S,5R,6S,7R,8S,9S)-7-acetoxy-9-benzyloxymethoxy-5-tert-butoxycarbonylamino-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-8-hydroxy-2-oxa-bicyclo[3.3.1]non-3-en-8-ylmethyl ester

Benzoic acid (1S,2R,3S,4R,5S,6R)-2-acetoxy-5-benzyloxymethoxy-4-tert-butoxycarbonylamino-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-(2-hydroxy-ethyl)-7-oxa-bicyclo[4.1.0]hept-1-ylmethyl ester