Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

Base Information

Chemical Name:Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside
CAS No.:111193-26-1
Molecular Formula:C₃₄H₄₅Cl₇N₂O₁₄
Molecular Weight:953.907
Hs Code.:

Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

Synonyms:Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

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Chemical Property of Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

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Technology Process of Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

There total 13 articles about Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-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: 76.0%

: 111193-25-0
Allyl 4-O-benzyl-6-O-(3,4,6-tri-O-acetyl-2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

: 111193-26-1
Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: With methanol; ammonium hydroxide; Ambient temperature;
DOI:10.1248/cpb.39.288

Reference yield:

: 66270-36-8
2,2,2-trichloro-1,1-dimethylethoxychloroformate

: 111193-26-1
Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent

2: 62 percent / HCl / 1.5 h / 100 °C

3: 82 percent / TsOH / dimethylformamide / 5 h / Ambient temperature

4: 94 percent / 4-dimethylaminopyridine / pyridine / 11 h / Ambient temperature

5: 83 percent / acetic acid / 0.25 h / 90 °C

6: 77 percent / pyridine / CH₂Cl₂ / 7 h / 0 °C

7: 83 percent / trifluoromeyhanesulfonic acid / CH₂Cl₂ / 48 h / Ambient temperature

8: 57 percent / NH₄OH / methanol; H₂O

9: 80 percent / FeCl₃, N,N,N',N'-tetramethylurea, Molecular Sieves 4A / CH₂Cl₂ / 48 h / Ambient temperature

10: 76 percent / NH₄OH / methanol; H₂O

With pyridine; hydrogenchloride; dmap; ammonium hydroxide; trifluorormethanesulfonic acid; 4 A molecular sieve; iron(III) chloride; toluene-4-sulfonic acid; acetic acid; tetramethylurea; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 111193-26-1
Allyl 4-O-benzyl-6-O-(2-chloroacetylamino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloro-tert-butoxycarbonylamino)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent

2: 62 percent / HCl / 1.5 h / 100 °C

3: 82 percent / TsOH / dimethylformamide / 5 h / Ambient temperature

4: 94 percent / 4-dimethylaminopyridine / pyridine / 11 h / Ambient temperature

5: 83 percent / acetic acid / 0.25 h / 90 °C

6: 77 percent / pyridine / CH₂Cl₂ / 7 h / 0 °C

7: 83 percent / trifluoromeyhanesulfonic acid / CH₂Cl₂ / 48 h / Ambient temperature

8: 57 percent / NH₄OH / methanol; H₂O

9: 80 percent / FeCl₃, N,N,N',N'-tetramethylurea, Molecular Sieves 4A / CH₂Cl₂ / 48 h / Ambient temperature

10: 76 percent / NH₄OH / methanol; H₂O

With pyridine; hydrogenchloride; dmap; ammonium hydroxide; trifluorormethanesulfonic acid; 4 A molecular sieve; iron(III) chloride; toluene-4-sulfonic acid; acetic acid; tetramethylurea; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;