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

Base Information

Chemical Name:((1R,2S,3R,4R,5S,6S)-2-Benzyloxymethoxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-6-hydroxymethyl-3-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamic acid tert-butyl ester
CAS No.:588693-85-0
Molecular Formula:C₄₇H₅₇NO₁₁
Molecular Weight:811.97
Hs Code.:

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

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

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

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

There total 20 articles about ((1R,2S,3R,4R,5S,6S)-2-Benzyloxymethoxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-6-hydroxymethyl-3-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamic acid tert-butyl 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: 98.0%

: 588693-83-8
((1R,2R,5S,6R)-2-Benzyloxymethoxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-4-hydroxymethyl-1-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-cyclohex-3-enyl)-carbamic acid tert-butyl ester

: 588693-85-0
((1R,2S,3R,4R,5S,6S)-2-Benzyloxymethoxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-6-hydroxymethyl-3-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamic acid tert-butyl ester

Guidance literature:: With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 20 ℃; for 12h;
DOI:10.1021/ja0342998

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 588693-85-0
((1R,2S,3R,4R,5S,6S)-2-Benzyloxymethoxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-6-hydroxymethyl-3-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 19 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

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:

: 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

: 588693-85-0
((1R,2S,3R,4R,5S,6S)-2-Benzyloxymethoxy-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxy-6-hydroxymethyl-3-{2-[(4-methoxy-phenyl)-diphenyl-methoxy]-ethyl}-7-oxa-bicyclo[4.1.0]hept-3-yl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

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