1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose

Base Information

Chemical Name:1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose
CAS No.:138312-57-9
Molecular Formula:C₃₇H₄₇NO₈Si
Molecular Weight:661.868
Hs Code.:

Synonyms:1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose

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Chemical Property of 1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose

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Technology Process of 1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose

There total 8 articles about 1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose 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:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 138312-57-9
1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / imidazole / dimethylformamide

2: 70 percent / DIBAL / diethyl ether; toluene / 1 h / temperature below -70 deg C

3: 1. ZnBr₂, 2. trifluoroacetic acid (TFA) / 1. THF, r.t., overnight; 2. CH₂Cl₂, 5 min

4: 97 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; methanol / 1 h / -78 °C

5: 94 percent / OsO₄, 4-methylmorpholine N-oxide monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol / 10 h / Ambient temperature

6: K₂CO₃ / methanol / 2 h

7: p-toluenesulfonic acid / various solvent(s) / 10 h

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine 4-oxide monohydrate; trifluoroacetic acid; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1021/jo00026a031

Reference yield:

: 122051-27-8
N-(Benzyloxycarbonyl)-O-(tert-butyldiphenylsilyl)-L-serinal

: 138312-57-9
1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose

Guidance literature:: Multi-step reaction with 5 steps

1: 1. ZnBr₂, 2. trifluoroacetic acid (TFA) / 1. THF, r.t., overnight; 2. CH₂Cl₂, 5 min

2: 97 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; methanol / 1 h / -78 °C

3: 94 percent / OsO₄, 4-methylmorpholine N-oxide monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol / 10 h / Ambient temperature

4: K₂CO₃ / methanol / 2 h

5: p-toluenesulfonic acid / various solvent(s) / 10 h

With sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine 4-oxide monohydrate; trifluoroacetic acid; zinc dibromide; In tetrahydrofuran; methanol; ethanol; tert-butyl alcohol;
DOI:10.1021/jo00026a031

Reference yield:

: 135245-97-5
methyl (2S)-3-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)-2-[(phenylmethoxy)carbonylamino]propanoate

: 138312-57-9
1,2:3,4-Di-O-isopropylidene-6-(N-(benzyloxycarbonyl)amino)-6-deoxy-7-O-(tert-butyldiphenylsilyl)-L-glycero-α-D-galacto-heptopyranose

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / DIBAL / diethyl ether; toluene / 1 h / temperature below -70 deg C

2: 1. ZnBr₂, 2. trifluoroacetic acid (TFA) / 1. THF, r.t., overnight; 2. CH₂Cl₂, 5 min

3: 97 percent / CeCl₃*7H₂O, NaBH₄ / ethanol; methanol / 1 h / -78 °C

4: 94 percent / OsO₄, 4-methylmorpholine N-oxide monohydrate / tetrahydrofuran; 2-methyl-propan-2-ol / 10 h / Ambient temperature

5: K₂CO₃ / methanol / 2 h

6: p-toluenesulfonic acid / various solvent(s) / 10 h

With sodium tetrahydroborate; osmium(VIII) oxide; cerium(III) chloride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine 4-oxide monohydrate; trifluoroacetic acid; zinc dibromide; In tetrahydrofuran; methanol; diethyl ether; ethanol; toluene; tert-butyl alcohol;
DOI:10.1021/jo00026a031