(2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid
• CAS No.: 100752-72-5
• Molecular Formula: C₄₆H₅₀N₆O₁₄
• Molecular Weight: 910.935
• Mol file: 100752-72-5.mol

Synonyms:

Chemical Property of (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid

There total 11 articles about (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid 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:

O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (99541-27-2) → (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid (100752-72-5)

Guidance literature:

With sodium hydroxide; In methanol; water; 1.) 0-5 deg C 2.) r.t., 3 h;

DOI:10.1016/S0008-6215(00)90458-0

Reference yield:

O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose (87907-02-6) → (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid (100752-72-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 71 percent / thiourea / ethanol / 6 h / Heating

2: 69 percent Turnov_. / mercuric bromide, molecular sieves 4A / CH₂Cl₂ / 72 h / Ambient temperature

3: M sodium hydroxide / methanol; H₂O / 1.) 0-5 deg C 2.) r.t., 3 h

With sodium hydroxide; 4 A molecular sieve; thiourea; mercury dibromide; In methanol; ethanol; dichloromethane; water;

DOI:10.1016/S0008-6215(00)90458-0

Reference yield:

O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose (99541-22-7) → (2S,3S,4S,5R,6R)-3-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-6-((1R,2S,3R,4R,5R)-4-azido-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid (100752-72-5)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium azide, ammonium chloride / dimethylformamide; H₂O / 37 h / 100 °C

2: pyridine / CH₂Cl₂ / 1.) 0-5 deg C 2.) r.t., 3 h

3: 94 percent / cupric chloride dihydrate / various solvent(s); ethanol / 1 h / Heating

4: pyridine / 4 h / 85 °C

5: pyridine / 1.) 0-5 deg C 2.) r.t., 30 min

6: Jones's reagent (4M chromium trioxide) / acetone / 1.) 0-5 deg C 2.) r.t., 50 min

7: CH₂Cl₂; diethyl ether

8: 71 percent / thiourea / ethanol / 6 h / Heating

9: 69 percent Turnov_. / mercuric bromide, molecular sieves 4A / CH₂Cl₂ / 72 h / Ambient temperature

10: M sodium hydroxide / methanol; H₂O / 1.) 0-5 deg C 2.) r.t., 3 h

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium azide; 4 A molecular sieve; ammonium chloride; thiourea; mercury dibromide; copper dichloride; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0008-6215(00)90458-0

upstream raw materials:

O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

O-(methyl 2,3-di-O-benzyl-4-O-(chloroacetyl)-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

O-(2,3-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Downstream raw materials:

O-(2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose