tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside
CAS No.:116103-00-5
Molecular Formula:C₄₇H₆₇N₃O₁₂Si
Molecular Weight:894.147
Hs Code.:

tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside

There total 10 articles about tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-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:

: 122350-80-5
1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol

: 116103-00-5
tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) DMF, -10 deg, 15 min, 2.) room temperature, 24 h

2: 56 percent / sodium azide, ceric ammonium nitrate / acetonitrile / 48 h / -20 °C

3: 76 percent / imidazole / CH₂Cl₂ / 24 h / Ambient temperature

4: 73 percent / aq. 10percent trifluoroacetic acid / CH₂Cl₂ / 20 h

5: 96 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

6: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) 0 deg, 15 h

7: 48 percent / NaNO₂ / acetic acid; acetic anhydride / 16 h / 0 °C

8: diethyl ether / 2 h / Ambient temperature

With pyridine; 1H-imidazole; sodium azide; ammonium cerium(IV) nitrate; sodium hydride; trifluoroacetic acid; sodium nitrite; In diethyl ether; dichloromethane; acetic anhydride; acetic acid; acetonitrile;
DOI:10.1016/0008-6215(90)84198-4

Reference yield:

: 129891-66-3
2-azido-2-deoxy-3,4-O-dibenzyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

: 116103-00-5
tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

2: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) 0 deg, 15 h

3: 48 percent / NaNO₂ / acetic acid; acetic anhydride / 16 h / 0 °C

4: diethyl ether / 2 h / Ambient temperature

With pyridine; sodium hydride; sodium nitrite; In diethyl ether; dichloromethane; acetic anhydride; acetic acid;
DOI:10.1016/0008-6215(90)84198-4

Reference yield:

: 129870-14-0
3,4-di-O-benzyl-6-O-trityl-D-glucal

: 116103-00-5
tert-butyldimethylsilyl 2-azido-3,4-di-O-benzyl-2-deoxy-6-O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-α-D-manno-2-octulopyranosylonate)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 56 percent / sodium azide, ceric ammonium nitrate / acetonitrile / 48 h / -20 °C

2: 76 percent / imidazole / CH₂Cl₂ / 24 h / Ambient temperature

3: 73 percent / aq. 10percent trifluoroacetic acid / CH₂Cl₂ / 20 h

4: 96 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

5: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) 0 deg, 15 h

6: 48 percent / NaNO₂ / acetic acid; acetic anhydride / 16 h / 0 °C

7: diethyl ether / 2 h / Ambient temperature

With pyridine; 1H-imidazole; sodium azide; ammonium cerium(IV) nitrate; sodium hydride; trifluoroacetic acid; sodium nitrite; In diethyl ether; dichloromethane; acetic anhydride; acetic acid; acetonitrile;
DOI:10.1016/0008-6215(90)84198-4