(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 104139-79-9
• Molecular Formula: C₄₅H₄₆ClN₃O₁₄
• Molecular Weight: 888.325

Synonyms:

Chemical Property of (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 18 articles about (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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: 20.0%

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R)-2-Acetoxymethyl-5-azido-4-benzyloxy-6-bromo-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104545-76-8) + benzyl alcohol (100-51-6,185532-71-2) → (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104139-79-9) + (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:

With 4 A molecular sieve; mercury dibromide; In 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)84054-X

Reference yield:

1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose (97390-18-6) → (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104139-79-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 1) Bu₂SnO, 2) Bu₄NI / 1) toluene, 2) 100 deg C

3: F^(1-) / in aqueous media

4: by tosylation

5: NaH

6: N₃^(1-)

7: by benzylation

9: by tosylation

10: NaI

11: DBU

12: 2) H₂O₂, aq. NaHCO₃ / 1) hydroboration, CH₂Cl₂

14: CrO₃-3.5 M H₂SO₄ / acetone

16: 94 percent / by acetolysis

17: TiBr₄

18: 20 percent / HgBr₂, molecular sieves (4 Angstroem) / 1,2-dichloro-ethane

With chromium(VI) oxide; 4 A molecular sieve; sulfuric acid; fluoride; dihydrogen peroxide; azide^(1-); titanium(IV) bromide; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; mercury dibromide; In 1,2-dichloro-ethane; acetone;

DOI:10.1016/S0040-4039(00)84054-X

Reference yield:

O-(2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose (115997-40-5) → (2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (104139-79-9)

Guidance literature:

Multi-step reaction with 13 steps

1: N₃^(1-)

2: by benzylation

4: by tosylation

5: NaI

6: DBU

7: 2) H₂O₂, aq. NaHCO₃ / 1) hydroboration, CH₂Cl₂

9: CrO₃-3.5 M H₂SO₄ / acetone

11: 94 percent / by acetolysis

12: TiBr₄

13: 20 percent / HgBr₂, molecular sieves (4 Angstroem) / 1,2-dichloro-ethane

With chromium(VI) oxide; 4 A molecular sieve; sulfuric acid; dihydrogen peroxide; azide^(1-); titanium(IV) bromide; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; mercury dibromide; In 1,2-dichloro-ethane; acetone;

DOI:10.1016/S0040-4039(00)84054-X

upstream raw materials:

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R)-2-Acetoxymethyl-5-azido-4-benzyloxy-6-bromo-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-(2-chloro-acetoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

benzyl alcohol

1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose

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

Downstream raw materials:

(2R,3S,4S,5R,6R)-6-((2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-azido-4,6-bis-benzyloxy-tetrahydro-pyran-3-yloxy)-5-benzoyloxy-4-benzyloxy-3-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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