methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Base Information

Chemical Name:methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside
CAS No.:473542-39-1
Molecular Formula:C₅₇H₆₇N₃O₁₃Si
Molecular Weight:1030.26
Hs Code.:

Synonyms:methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

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Chemical Property of methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

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Technology Process of methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

There total 7 articles about methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-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: 72.0%

: 189182-66-9
2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranosyl trichloroacetimidate

: 473542-37-9
methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

: 473542-39-1
methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -40 ℃; for 0.5h;
DOI:10.1002/1099-0690(200207)2002:13<2033::AID-EJOC2033>3.0.CO;2-W

Reference yield: 56.0%

: Acetic acid (3R,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester

: 473542-37-9
methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

: 473542-39-1
methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1002/1099-0690(200207)2002:13<2033::AID-EJOC2033>3.0.CO;2-W

Reference yield:

: 87038-18-4
methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 473542-39-1
methyl 4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 3.28 g / Ba(OH)2*8H₂O / H₂O; methanol / 18 h / 100 °C

2: 73 percent / TfN₃; 4-(dimethylamino)pyridine / methanol / 18 h / 20 °C

3: 99 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / pyridine / 18 h / 20 °C

4: 81 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

5: 72 percent / imidazole / dimethylformamide / 18 h / 20 °C

6: 72 percent / molecular sieves 4A; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -40 °C

With 1H-imidazole; dmap; barium dihydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; triflic azide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200207)2002:13<2033::AID-EJOC2033>3.0.CO;2-W