tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 937394-26-8
• Molecular Formula: C₅₉H₆₉N₄O₁₆PSi
• Molecular Weight: 1149.27

Synonyms:tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

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Technology Process of tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 15 articles about tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-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: 79.0%

3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3yl)-2-(9-fluorenylmethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate (937394-25-7) + tert-butyldimethylsilyl 2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-21-3) → tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-26-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -60 ℃; for 0.25h;

DOI:10.1021/ja068922a

Reference yield: 40.0%

tert-butyldimethylsilyl 2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-21-3) + C42H40Cl3N2O12P → tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-26-8)

Guidance literature:

tert-butyldimethylsilyl 2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside; C₄₂H₄₀Cl₃N₂O₁₂P; In dichloromethane; at 20 ℃; for 1h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -60 ℃; for 0.5h; Molecular sieve;

Reference yield:

tert-butyldimethylsilyl 3-O-allyloxycarbonyl-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-22-4) → tert-butyldimethylsilyl-6-O-[3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranosyl]-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside (937394-26-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-tetrazole / CH₂Cl₂ / 0.25 h / 20 °C

1.2: 89 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.33 h / -20 °C

2.1: acetic acid; zinc / CH₂Cl₂ / 2 h / 20 °C

3.1: 1.45 g / N,N-diisopropylethylamine / CH₂Cl₂ / 5 h / 0 - 20 °C

4.1: 98 percent / HF*pyridine / tetrahydrofuran / 12 h / 20 °C

5.1: 92 percent / NaH / CH₂Cl₂ / 0.83 h / 20 °C

6.1: 79 percent / molecular sieves 4 Angstroem; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.25 h / -60 °C

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja068922a

upstream raw materials:

3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-2-(9-fluorenylmethoxycarbonylamino)-D-glucopyranosyl trichloroacetimidate

tert-butyldimethylsilyl 2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

t-butyldimethylsilyl 3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ⁵-3H-2,4,3-benzodioxaphosphepin-3yl)-2-(9-fluorenylmethoxycarbonylamino)-β-D-glucopyranoside

C₄₀H₄₀NO₁₂P

Downstream raw materials:

C₄₄H₅₉N₄O₁₄PSi

tert-butyldimethylsilyl 6-O-{3-O-allyloxycarbonyl-6-O-benzyl-2-deoxy-4-O-(1,5-dihydro-3-oxo-3λ5-3H-2,4,3-benzodioxaphosphepin-3-yl)-2-[(R)-3-dodecanoyloxy-tetradecanoylamino]-β-D-glucopyranosyl}-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranoside

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