Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester

Base Information

Chemical Name:Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester
CAS No.:459170-66-2
Molecular Formula:C₃₂H₃₃F₃NO₁₁P
Molecular Weight:695.583
Hs Code.:

Synonyms:Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester

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Chemical Property of Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester

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Technology Process of Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester

There total 5 articles about Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl 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:

: 459170-53-7
4-O-acetyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-5,6-didehydro-2-trifluoroacetamido-α-D-glucopyranosyl 1-dibenzyl phosphate

: 459170-66-2
Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester

Guidance literature:: With 3,3-dimethyldioxirane; In dichloromethane; for 17.5h;
DOI:10.1021/ja0127234

Reference yield:

: 990-91-0
dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

: 459170-66-2
Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 84 percent / tetrahydrofuran; hexane / 2.33 h / -78 - 0 °C

2.1: NaIO₄; aq. NaHCO₃ / methanol / 1.5 h

3.1: 480 mg / dihydropyran / 4.75 h / Heating

4.1: dimethyldioxirane / CH₂Cl₂ / 17.5 h

With 3,4-dihydro-2H-pyran; sodium periodate; 3,3-dimethyldioxirane; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ja0127234

Reference yield:

: 4-O-acetyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-phenylseleno-2-trifluoroacetamido-D-glucopyranose

: 459170-66-2
Acetic acid (5R,6R,7R,8S)-7-benzyloxymethoxy-5-(bis-benzyloxy-phosphoryloxy)-6-(2,2,2-trifluoro-acetylamino)-1,4-dioxa-spiro[2.5]oct-8-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: 84 percent / tetrahydrofuran; hexane / 2.33 h / -78 - 0 °C

2.1: NaIO₄; aq. NaHCO₃ / methanol / 1.5 h

3.1: 480 mg / dihydropyran / 4.75 h / Heating

4.1: dimethyldioxirane / CH₂Cl₂ / 17.5 h

With 3,4-dihydro-2H-pyran; sodium periodate; 3,3-dimethyldioxirane; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;
DOI:10.1021/ja0127234