Carbamic acid, [(1S,4S,5S,6S,7R,8S,9S)-7-(acetyloxy)-8-[(benzoyloxy)methyl]-6-[(4S)- 2,2-dimethyl-1,3-dioxolan-4-yl]-4,8-dihydroxy-3-oxo-9-[(phenylmethoxy) methoxy]-2-oxabicyclo[3.3.1]non-5-yl]-, 1,1-dimethylethyl ester

Base Information

Chemical Name:Carbamic acid, [(1S,4S,5S,6S,7R,8S,9S)-7-(acetyloxy)-8-[(benzoyloxy)methyl]-6-[(4S)- 2,2-dimethyl-1,3-dioxolan-4-yl]-4,8-dihydroxy-3-oxo-9-[(phenylmethoxy) methoxy]-2-oxabicyclo[3.3.1]non-5-yl]-, 1,1-dimethylethyl ester
CAS No.:588694-06-8
Molecular Formula:C36H45NO14
Molecular Weight:715.752
Hs Code.:

Carbamic acid,
[(1S,4S,5S,6S,7R,8S,9S)-7-(acetyloxy)-8-[(benzoyloxy)methyl]-6-[(4S)-
2,2-dimethyl-1,3-dioxolan-4-yl]-4,8-dihydroxy-3-oxo-9-[(phenylmethoxy)
methoxy]-2-oxabicyclo[3.3.1]non-5-yl]-, 1,1-dimethylethyl ester

Synonyms:

Suppliers and Price of Carbamic acid, [(1S,4S,5S,6S,7R,8S,9S)-7-(acetyloxy)-8-[(benzoyloxy)methyl]-6-[(4S)- 2,2-dimethyl-1,3-dioxolan-4-yl]-4,8-dihydroxy-3-oxo-9-[(phenylmethoxy) methoxy]-2-oxabicyclo[3.3.1]non-5-yl]-, 1,1-dimethylethyl ester

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Chemical Property of Carbamic acid, [(1S,4S,5S,6S,7R,8S,9S)-7-(acetyloxy)-8-[(benzoyloxy)methyl]-6-[(4S)- 2,2-dimethyl-1,3-dioxolan-4-yl]-4,8-dihydroxy-3-oxo-9-[(phenylmethoxy) methoxy]-2-oxabicyclo[3.3.1]non-5-yl]-, 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of Carbamic acid, [(1S,4S,5S,6S,7R,8S,9S)-7-(acetyloxy)-8-[(benzoyloxy)methyl]-6-[(4S)- 2,2-dimethyl-1,3-dioxolan-4-yl]-4,8-dihydroxy-3-oxo-9-[(phenylmethoxy) methoxy]-2-oxabicyclo[3.3.1]non-5-yl]-, 1,1-dimethylethyl ester

There total 30 articles about Carbamic acid, [(1S,4S,5S,6S,7R,8S,9S)-7-(acetyloxy)-8-[(benzoyloxy)methyl]-6-[(4S)- 2,2-dimethyl-1,3-dioxolan-4-yl]-4,8-dihydroxy-3-oxo-9-[(phenylmethoxy) methoxy]-2-oxabicyclo[3.3.1]non-5-yl]-, 1,1-dimethylethyl 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:

: 3587-60-8
Benzyloxymethyl chloride

: 588694-06-8
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

Guidance literature:: Multi-step reaction with 29 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

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

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

28.1: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C

29.1: NaBH₄ / methanol / 0.25 h / -78 °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; 10-camphorsufonic acid; potassium tert-butylate; tetrabutyl-ammonium chloride; magnesium ethylate; pyridinium p-toluenesulfonate; acetic anhydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 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; water; sodium hydrogencarbonate; dimethyl sulfoxide; ethyl acetate; 1,2-dichloro-ethane; 1,2-dichloro-benzene; acetone; tert-butyl alcohol; benzene; 21.1: Albright-Goldman reaction;
DOI:10.1021/ja0342998

Reference yield:

: 588694-04-6
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

: 588694-06-8
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

Guidance literature:: With sodium tetrahydroborate; In methanol; at -78 ℃; for 0.25h;
DOI:10.1021/ja0342998

Reference yield:

: 588693-71-4
(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

: 588694-06-8
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

Guidance literature:: Multi-step reaction with 21 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

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

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

20: 141 mg / o-iodoxybenzoic acid / dimethylsulfoxide / 0.42 h / 55 °C

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

With pyridine; 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; 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; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; sodium hydrogencarbonate; dimethyl sulfoxide; 1,2-dichloro-ethane; 1,2-dichloro-benzene; acetone; tert-butyl alcohol; benzene; 13: Albright-Goldman reaction;
DOI:10.1021/ja0342998