N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 143419-04-9
• Molecular Formula: C₂₉H₃₈N₄O₁₀
• Molecular Weight: 602.642

Synonyms:

Chemical Property of N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide

There total 15 articles about N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide 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:

2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide (34339-69-0) → N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (143419-04-9)

Guidance literature:

Multi-step reaction with 12 steps

1: Koenigs-Knorr type conditions

2: Et₃N / H₂O; methanol / 26 h / 4 °C

3: 77 percent / p-toluenesulfonic acid / acetonitrile

4: sodium cyanoborohydride, HCl

6: azide

7: tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclooctane

8: HgCl₂, HgO / hydrolysis

9: oxalyl bromide / dimethylformamide

10: 71 percent / Hg(CN)2

11: deacetylation

12: 79percent aq. HOAc / 70 °C

With hydrogenchloride; Wilkinson's catalyst; 1,4-diazabicyclooctane; Oxalyl bromide; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; mercury dichloride; mercury(II) oxide; In methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(90)80170-8

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (143419-04-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / p-toluenesulfonic acid / acetonitrile

2: sodium cyanoborohydride, HCl

4: azide

5: tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclooctane

6: HgCl₂, HgO / hydrolysis

7: oxalyl bromide / dimethylformamide

8: 71 percent / Hg(CN)2

9: deacetylation

10: 79percent aq. HOAc / 70 °C

With hydrogenchloride; Wilkinson's catalyst; 1,4-diazabicyclooctane; Oxalyl bromide; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(90)80170-8

Reference yield:

allyl 2-O-acetyl-3-O-benzyl-β-D-glucopyranoside (143419-08-3) → N-[(2R,3R,4R,5S,6R)-4-((2S,3R,4S,5S,6S)-5-Azido-4-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl]-acetamide (143419-04-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / p-toluenesulfonic acid / acetonitrile

2: sodium cyanoborohydride, HCl

4: azide

5: tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclooctane

6: HgCl₂, HgO / hydrolysis

7: oxalyl bromide / dimethylformamide

8: 71 percent / Hg(CN)2

9: deacetylation

10: 79percent aq. HOAc / 70 °C

With hydrogenchloride; Wilkinson's catalyst; 1,4-diazabicyclooctane; Oxalyl bromide; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; mercury dichloride; mercury(II) oxide; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0008-6215(90)80170-8

upstream raw materials:

2,4,6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl bromide

benzaldehyde dimethyl acetal

methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

allyl 2-O-acetyl-3-O-benzyl-β-D-glucopyranoside

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