Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Base Information

Chemical Name:Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester
CAS No.:214619-40-6
Molecular Formula:C₂₃H₃₉NO₈SSi
Molecular Weight:517.716
Hs Code.:

Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Synonyms:Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

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Chemical Property of Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

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Technology Process of Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

There total 10 articles about Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl 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: 96.0%

: 124-63-0
methanesulfonyl chloride

: 214619-44-0
{(4R,5R)-5-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl}-carbamic acid benzyl ester

: 214619-40-6
Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Guidance literature:: With triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1039/a803342k

Reference yield:

: 19139-74-3
2,3:4,5-di-O-isopropylidene-D-arabinitol

: 214619-40-6
Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / Et₃N / tetrahydrofuran / 1 h / 0 °C

2: NaN₃ / dimethylformamide / 60 °C

3: H₂ / 10percent Pd/C / ethyl acetate / 6 h

4: K₂CO₃, H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 95 percent / Dowex 50W-X₈ / methanol; H₂O / 18 h / Ambient temperature

6: 96 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

7: 96 percent / Et₃N / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium azide; Dowex 50W-X₈; water; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/a803342k

Reference yield:

: 72551-02-1
2,3:4,5-Di-O-isopropylidene-1-O-methylsulfonyl-D-arabinitol

: 214619-40-6
Methanesulfonic acid (R)-1-[(4S,5R)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: NaN₃ / dimethylformamide / 60 °C

2: H₂ / 10percent Pd/C / ethyl acetate / 6 h

3: K₂CO₃, H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 95 percent / Dowex 50W-X₈ / methanol; H₂O / 18 h / Ambient temperature

5: 96 percent / imidazole / dimethylformamide / 6 h / Ambient temperature

6: 96 percent / Et₃N / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; sodium azide; Dowex 50W-X₈; water; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/a803342k