3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester

Base Information

Chemical Name:3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester
CAS No.:503311-37-3
Molecular Formula:C₂₉H₃₇NO₈Si
Molecular Weight:555.7
Hs Code.:

Synonyms:3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester

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Chemical Property of 3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester

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Technology Process of 3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester

There total 1 articles about 3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl 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: 75.0%

: 438547-22-9
3-Benzyloxy-5-nitro-4-trifluoromethanesulfonyloxy-benzoic acid methyl ester

: 360562-49-8
5-[(tert-Butyldimethylsilyl)oxy]-1,2-dideoxy-3,4-O-(1-methylethylidene)-L-threo-pent-1-yne

: 503311-37-3
3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester

Guidance literature:: With palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; at 20 - 65 ℃; for 13h;
DOI:10.1002/anie.200290016

Reference yield:

: 503311-37-3
3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester

: 7-benzyloxy-8-hydroxymethyl-3-(1-methoxy-1-methyl-ethoxy)-9-oxo-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 15 steps

1: benzene / 1 h / 20 °C

2: aq. AcOH / 2 h / 20 °C

3: 94 percent / Zn(BH₄)2 / diethyl ether / 3 h / -30 °C

4: 2,6-lutidine / CH₂Cl₂ / 7 h / 20 °C

5: aq. AcOH / dimethyl ether / 4 h

6: Et₃N; DMAP / CH₂Cl₂ / 13 h / 20 °C

7: DABCO / CH₂Cl₂ / 1.5 h / 20 °C

8: NaH / dimethylformamide / 0.5 h / 0 - 20 °C

9: 10-camphorsulfonic acid / methanol / 1 h / 20 °C

10: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 - 20 °C

11: H₂ / Pd/C / methanol / 2 h / 20 °C

12: TsOH*H₂O / CH₂Cl₂ / 0.17 h / 20 °C

13: TBAF / tetrahydrofuran / 20 °C

14: 82 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 20 °C

15: aq. LiOH / tetrahydrofuran / 5 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; dmap; lithium hydroxide; zinc(II) tetrahydroborate; oxalyl dichloride; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; Dimethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 10: Dess-Martin oxidation / 14: Swern oxidation;
DOI:10.1002/anie.200290016

Reference yield:

: 503311-37-3
3-Benzyloxy-4-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylethynyl]-5-nitro-benzoic acid methyl ester

: 503311-47-5
7-benzyloxy-3-hydroxy-9-triisopropylsilanyloxy-1a,2,3,8,9,9a-hexahydro-1-oxa-3-aza-benzo[a]cyclopropa[e]cyclooctene-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: benzene / 1 h / 20 °C

2: aq. AcOH / 2 h / 20 °C

3: 94 percent / Zn(BH₄)2 / diethyl ether / 3 h / -30 °C

4: 2,6-lutidine / CH₂Cl₂ / 7 h / 20 °C

5: aq. AcOH / dimethyl ether / 4 h

6: Et₃N; DMAP / CH₂Cl₂ / 13 h / 20 °C

7: DABCO / CH₂Cl₂ / 1.5 h / 20 °C

8: NaH / dimethylformamide / 0.5 h / 0 - 20 °C

9: 10-camphorsulfonic acid / methanol / 1 h / 20 °C

10: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 - 20 °C

11: H₂ / Pd/C / methanol / 2 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; dmap; zinc(II) tetrahydroborate; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydride; Dess-Martin periodane; acetic acid; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; Dimethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 10: Dess-Martin oxidation;
DOI:10.1002/anie.200290016