methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

Base Information

Chemical Name:methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside
CAS No.:116405-18-6
Molecular Formula:C₃₅H₄₂NO₁₉S*Na
Molecular Weight:835.77
Hs Code.:

Synonyms:methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

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Chemical Property of methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

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Technology Process of methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

There total 5 articles about methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-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: 93.0%

: 116386-36-8
methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

: 116405-18-6
methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

Guidance literature:: With Sephadex SP-C₂₅ (Na⁽¹⁺⁾-form); sulfur trioxide trimethylamine complex; In N,N-dimethyl-formamide; at 60 ℃; for 1.5h;
DOI:10.1016/0008-6215(88)85095-X

Reference yield:

: 108032-44-6
methyl (2,3,4-tetra-O-acetyl-α-L-idopyranosyl bromide)uroate

: 116405-18-6
methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 83 percent / molecular sieves 4 A, silver triflate / 1,2-dichloro-ethane / 1.) 15 min, RT; 2.) 1 h, -20 deg C; 3.) to RT, 3 h

2: 89 percent / thiourea / pyridine; ethanol / 0.75 h / 100 °C

3: 93 percent / 1.) sulfur trioxide-trimethylamine complex; 2.) Sephadex SP-C₂₅ (Na⁽¹⁺⁾-form) / dimethylformamide / 1.5 h / 60 °C

With 4 A molecular sieve; Sephadex SP-C₂₅ (Na⁽¹⁺⁾-form); silver trifluoromethanesulfonate; sulfur trioxide trimethylamine complex; thiourea; In pyridine; ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(88)85095-X

Reference yield:

: 87907-35-5
methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside

: 116405-18-6
methyl 3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2,3,4-tri-O-acetyl-α-L-idopyranosyluronate)-6-O-sulfo-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 83 percent / molecular sieves 4 A, silver triflate / 1,2-dichloro-ethane / 1.) 15 min, RT; 2.) 1 h, -20 deg C; 3.) to RT, 3 h

3: 89 percent / thiourea / pyridine; ethanol / 0.75 h / 100 °C

4: 93 percent / 1.) sulfur trioxide-trimethylamine complex; 2.) Sephadex SP-C₂₅ (Na⁽¹⁺⁾-form) / dimethylformamide / 1.5 h / 60 °C

With pyridine; 4 A molecular sieve; Sephadex SP-C₂₅ (Na⁽¹⁺⁾-form); silver trifluoromethanesulfonate; sulfur trioxide trimethylamine complex; thiourea; In pyridine; ethanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(88)85095-X