methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside
• CAS No.: 498539-44-9
• Molecular Formula: C₅₀H₇₇NO₉Si₂
• Molecular Weight: 892.334

Synonyms:methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside

Chemical Property of methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside

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Technology Process of methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside

There total 6 articles about methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside 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:

[(3aR,4R,7S,7aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-benzo[1,3]dioxol-(5Z)-ylidene]-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl)-amine → methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside (498539-44-9) + methyl 6-{[(1'S,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside

Guidance literature:

With sodium cyanoborohydride; In ethanol; at 20 ℃; for 14h;

DOI:10.1016/j.tet.2003.09.049

Reference yield:

methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside (72471-11-5) + [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one (498539-40-5) → methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside (498539-44-9) + methyl 6-{[(1'S,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside

Guidance literature:

methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside; [3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one; With titanium(IV) isopropylate; In dichloromethane; at 20 ℃; for 2h;

With sodium cyanoborohydride; In ethanol; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(02)02016-6

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → methyl 6-{[(1'R,3'S,4'S,5'R,6'S)-3'-{tert-butyl(dimethyl)silyloxy}-6'-({tert-butyl(dimethyl)silyloxy}methyl)-4',5'-O-(1-methylethylidene)-3',4',5'-trihydroxycyclohexyl]amino}-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside (498539-44-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / imidazole / dimethylformamide / 24 h / 70 °C

2: 77 percent / N-bromosuccinimide / acetone; H₂O / 0.5 h / -25 °C

3: Ti(OiPr)4 / ethanol / 2 h / 20 °C

4: sodium cyanoborohydride / ethanol / 14 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; N-Bromosuccinimide; sodium cyanoborohydride; In ethanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2003.09.049

upstream raw materials:

methyl 6-deoxy-6-amino-2,3,4-tri-O-benzyl-α-D-glucopyranoside

[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-tert-butyl(dimethyl)silyloxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one

tert-butyldimethylsilyl chloride

[3S,4S,5R,6R]-3-O-tert-butyl(dimethyl)silyl-6-hydroxymethyl-4,5-O-(1-methylethylidene)-3,4,5-trihydroxycyclohexan-1-one 1,3-propanedithioketal

Downstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-{[(1R,2R,3R,4R,5S)-3,4,5-trihydroxy-2-(hydroxymethyl)cyclohexyl]amino}-α-D-glucopyranoside

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