1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

Base Information

Chemical Name:1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose
CAS No.:220109-94-4
Molecular Formula:C₂₉H₄₇NO₈Si
Molecular Weight:565.78
Hs Code.:

1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

Synonyms:1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

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Chemical Property of 1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

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Technology Process of 1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

There total 3 articles about 1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose 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:

: (2S,4R)-2-[(R)-((1R,3R,4R,5R)-4-Benzyloxy-2-oxo-6,8-dioxa-bicyclo[3.2.1]oct-3-yl)-hydroxy-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 220109-94-4
1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

Guidance literature:: With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at -40 - -20 ℃; for 20h;
DOI:10.1021/jo981781d

Reference yield:

: 33647-85-7
isolevoglucosenone

: 220109-94-4
1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: 90 percent / triethylamine / 15 h / 20 °C

2.1: potassium bis(trimethylsilyl)amide; ZnCl₂ / toluene; tetrahydrofuran; diethyl ether / 1.25 h / -78 - -50 °C

2.2: toluene; tetrahydrofuran; diethyl ether / 5 h / -78 - -45 °C

3.1: 32 mg / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 20 h / -40 - -20 °C

With potassium hexamethylsilazane; triethylamine; zinc(II) chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; acetic acid; toluene; acetonitrile; 1.1: Addition / 2.1: Metallation / 2.2: Addition / 3.1: Reduction;
DOI:10.1021/jo981781d

Reference yield:

: 123823-24-5
1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose

: 220109-94-4
1,6-anhydro-2-O-benzyl-3-deoxy-3-[(1'R)-4'-O-tert-butyldimethylsilyl-N-tert-butyloxycarbonyl-2',3',5'-trideoxy-2',5'-imino-L-erythro-pentitol-1'-C-yl]-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium bis(trimethylsilyl)amide; ZnCl₂ / toluene; tetrahydrofuran; diethyl ether / 1.25 h / -78 - -50 °C

1.2: toluene; tetrahydrofuran; diethyl ether / 5 h / -78 - -45 °C

2.1: 32 mg / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 20 h / -40 - -20 °C

With potassium hexamethylsilazane; zinc(II) chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; acetic acid; toluene; acetonitrile; 1.1: Metallation / 1.2: Addition / 2.1: Reduction;
DOI:10.1021/jo981781d