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

Base Information

• Chemical Name: 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
• CAS No.: 588693-98-5
• Molecular Formula: C₃₆H₄₅NO₁₂
• Molecular Weight: 683.753
• Mol file: 588693-98-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 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

There total 26 articles about 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 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: 100.0%

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 (588693-96-3) → 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 (588693-98-5)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 3h;

DOI:10.1021/ja0342998

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 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 (588693-98-5)

Guidance literature:

Multi-step reaction with 25 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

21.1: Ac₂O; DMSO / 2 h / 20 °C

22.1: 1.04 g / NaBH₄ / methanol / 0.25 h / 0 °C

23.1: 100 percent / DMAP / pyridine / 1.5 h / 20 °C

24.1: 89 percent / TFA / methanol / 3 h / 20 °C

25.1: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °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; acetic anhydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury(II) oxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; pyridine; methanol; dichloromethane; sodium hydrogencarbonate; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; acetone; tert-butyl alcohol; benzene; 21.1: 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) → 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 (588693-98-5)

Guidance literature:

Multi-step reaction with 17 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

13: Ac₂O; DMSO / 2 h / 20 °C

14: 1.04 g / NaBH₄ / methanol / 0.25 h / 0 °C

15: 100 percent / DMAP / pyridine / 1.5 h / 20 °C

16: 89 percent / TFA / methanol / 3 h / 20 °C

17: 100 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 3 h / 20 °C

With pyridine; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; disodium hydrogenphosphate; sodium dihydrogenphosphate; N-chloro-succinimide; lithium borohydride; 2-methyl-but-2-ene; potassium tert-butylate; tetrabutyl-ammonium chloride; acetic anhydride; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; pyridine; methanol; dichloromethane; sodium hydrogencarbonate; dimethyl sulfoxide; 1,2-dichloro-ethane; tert-butyl alcohol; benzene; 13: Albright-Goldman reaction;

DOI:10.1021/ja0342998

upstream raw materials:

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

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

Downstream raw materials:

tetradotoxin

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-3,4-dioxo-2-oxa-bicyclo[3.3.1]non-8-ylmethyl ester

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

C₃₆H₄₁NO₁₆