tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 116128-72-4
• Molecular Formula: C₆₇H₈₉N₇O₁₅Si
• Molecular Weight: 1260.57

Synonyms:

Chemical Property of tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 13 articles about tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-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:

1,5-anhydro-2-deoxy-6-O-trityl-D-arabino-hex-1-enitol (122350-80-5) → tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (116128-72-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) DMF, -10 deg, 15 min, 2.) room temperature, 24 h

2: 56 percent / sodium azide, ceric ammonium nitrate / acetonitrile / 48 h / -20 °C

3: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) -10 deg, 20 h, c) ambient temperature, 20 h

4: 55 percent / aq. 10percent trifluoroacetic acid / CH₂Cl₂

5: 98 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

6: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) -10 deg, 72 h

With pyridine; sodium azide; ammonium cerium(IV) nitrate; sodium hydride; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(90)84198-4

Reference yield:

2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trityl-α,β-D-glucopyranose → tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (116128-72-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) -10 deg, 20 h, c) ambient temperature, 20 h

2: 55 percent / aq. 10percent trifluoroacetic acid / CH₂Cl₂

3: 98 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

4: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) -10 deg, 72 h

With pyridine; sodium hydride; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/0008-6215(90)84198-4

Reference yield:

3,4-di-O-benzyl-6-O-trityl-D-glucal (129870-14-0) → tert-butyldimethylsilyl O-(4,5:7,8-di-O-cyclohexylidene-3-deoxy-N-methyl-α-D-manno-2-octulopyranosylonamide)-(2->6)-O-(2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->6)-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (116128-72-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 56 percent / sodium azide, ceric ammonium nitrate / acetonitrile / 48 h / -20 °C

2: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) -10 deg, 20 h, c) ambient temperature, 20 h

3: 55 percent / aq. 10percent trifluoroacetic acid / CH₂Cl₂

4: 98 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

5: 1.) NaH / 1.) THF, -30 deg, 20 min, 2.) a) -30 deg, 3 h, b) -10 deg, 72 h

With pyridine; sodium azide; ammonium cerium(IV) nitrate; sodium hydride; trifluoroacetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(90)84198-4

upstream raw materials:

C₂₁H₃₃NO₇

tert-butyldimethylsilyl 2-azido-6-O-(2-azido-3,4-di-O-benzyl-2-deoxy-6-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

cyclohexanone

3-deoxy-5,6:7,8-di-O-isopropylidene-D-manno-oct-2-enono-1,4-lactone

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