3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside

Base Information

Chemical Name:3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside
CAS No.:591229-74-2
Molecular Formula:C₅₈H₅₆ClIO₁₃
Molecular Weight:1123.43
Hs Code.:

Synonyms:3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside

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Chemical Property of 3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside

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Technology Process of 3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside

There total 9 articles about 3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-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: 70.0%

: 591229-68-4
3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-galactopyranoside

: 591229-74-2
3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside

Guidance literature:: 3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-galactopyranoside; With trifluoromethylsulfonic anhydride; In pyridine; dichloromethane; 195 K, 15 min, 273 K, 2 h;

With lithium chloride; In acetone;
DOI:10.1107/S0108270101009994

Reference yield:

: Acetic acid (2S,3R,4R,5R)-2-((2R,3R,4R,5S,6R)-3,4-diacetoxy-6-acetoxymethyl-5-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-yloxy)-4-iodo-2,5-bis-trityloxymethyl-tetrahydro-furan-3-yl ester

: 591229-74-2
3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside

Guidance literature:: With lithium chloride; In acetone; at 20 ℃; for 12h;
DOI:10.1081/CAR-120021700

Reference yield:

: 111829-04-0
3,4-anhydro-1,6-di-O-trityl-β-D-lyxo-hexulofuranosyl 2,3,4-tri-O-acetyl-6-O-trityl-α-D-glucopyranoside

: 591229-74-2
3-O-acetyl-4-deoxy-4-iodo-1,6-di-O-trityl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-4-chloro-4-deoxy-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 73 percent / NaI; AcOH / dimethylformamide / 110 °C

2: 87 percent / pyridine

3: 63 percent / aq. HCl; AcOH / CH₂Cl₂ / 1.5 h / 0 °C

4: AcOH / various solvent(s) / 8 h / Heating

5: 1.56 g / pyridine / 48 h / 80 °C

6: pyridine / CH₂Cl₂ / 2.25 h / -78 - 0 °C

7: 1.01 g / NaNO₂ / dimethylformamide / 20 °C

8: pyridine / CH₂Cl₂ / 2.25 h / -78 - 0 °C

9: 0.50 g / LiCl / acetone / 12 h / 20 °C

With pyridine; hydrogenchloride; acetic acid; sodium iodide; lithium chloride; sodium nitrite; In dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1081/CAR-120021700