Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside

Base Information

Chemical Name:Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside
CAS No.:175980-99-1
Molecular Formula:C₃₉H₅₀O₁₂S₃
Molecular Weight:807.017
Hs Code.:

Synonyms:Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside

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Chemical Property of Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside

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Technology Process of Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside

There total 17 articles about Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-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: 91.0%

: 175981-12-1
Heptyl 4-S-acetyl-2,6-di-O-benzoyl-3-thio-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-1,3,4-trithio-β-D-glucopyranoside

: 175980-99-1
Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside

Guidance literature:: With hydrazinium monoacetate; In N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00061-5

Reference yield:

: 175980-95-7
Acetic acid (2S,3R,4R,5S,6S)-3-acetoxy-5-(4-methoxy-benzyloxy)-2-methyl-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester

: 175980-99-1
Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 75 percent / TMSOTf / CH₂Cl₂ / -10 °C

2: 1.) ceric ammonium nitrate / 1.) CH₃CN/H₂O; 2.) pyridine

3: 1.) p-toluenesulfonic acid, ethylmercaptan; 2.) triethylamine / 2.) -17 degC

4: 1.) Tf₂O / 1.) pyridine, -17 degC; 2.) THF, r. t.

5: 1.) tetrabutylammonium fluoride; 2.) DBU / 1.) THF, -20 degC

6: 73 percent / BF₃*OEt₂

7: 91 percent / hydrazinium acetate / dimethylformamide

With ammonium cerium(IV) nitrate; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; hydrazinium monoacetate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; ethanethiol; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00061-5

Reference yield:

: 175981-10-9
Thexyldimethylsilyl 4-S-acetyl-2,6-di-O-benzoyl-3-S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-3,4-dithio-β-D-glucopyranoside

: 175980-99-1
Heptyl S-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-2,6-di-O-benzoyl-4-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) tetrabutylammonium fluoride; 2.) DBU / 1.) THF, -20 degC

2: 73 percent / BF₃*OEt₂

3: 91 percent / hydrazinium acetate / dimethylformamide

With tetrabutyl ammonium fluoride; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; boron trifluoride diethyl etherate; In N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00061-5