methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate

Base Information

• Chemical Name: methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate
• CAS No.: 114869-97-5
• Molecular Formula: C40H47 N O15
• Molecular Weight: 781.811
• European Community (EC) Number: 856-108-0
• Nikkaji Number: J1.195.442A
• Mol file: 114869-97-5.mol

Synonyms:114869-97-5;methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate;a-D-Glucopyranoside,methyl 4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deox;methyl (2R,3S,4S,5R,6R)-5-acetyloxy-6-[(2R,3S,4R,5R,6S)-2-(acetyloxymethyl)-6-methoxy-4-phenylmethoxy-5-(phenylmethoxycarbonylamino)oxan-3-yl]oxy-3-hydroxy-4-phenylmethoxyoxane-2-carboxylate;Fondaparinux sodium intermediate;SCHEMBL7464539;methyl (2R,3S,4S,5R,6R)-5-(acetyloxy)-6-{[(2R,3S,4R,5R,6S)-2-[(acetyloxy)methyl]-4-(benzyloxy)-5-{[(benzyloxy)carbonyl]amino}-6-methoxyoxan-3-yl]oxy}-4-(benzyloxy)-3-hydroxyoxane-2-carboxylate;a-D-Glucopyranoside,methyl 4-O-[2-O-acetyl-6-methyl-3-O-(phenylmethyl)-a-L-idopyranuronosyl]-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-,6-acetate;Methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-alpha-L-idopyranosyluronate)-alpha-D-glucopyranoside;Methyl 6-O-acetyl-4-O-(2-O-acetyl-3-O-benzyl-6-methyl-?-L-idopyra nuronosyl)-3-O-benzyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-?-D- glucopyranoside

Chemical Property of methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate

Chemical Property:

• PSA: 196.33000
• LogP: 3.16670
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 20
• Exact Mass: 781.29456979
• Heavy Atom Count: 56
• Complexity: 1240

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-alpha-L-idopyranosyluronate)-alpha-D-glucopyranoside min. 99% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC)NC(=O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OC4C(C(C(C(O4)C(=O)OC)O)OCC5=CC=CC=C5)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC)NC(=O)OCC2=CC=CC=C2)OCC3=CC=CC=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](O4)C(=O)OC)O)OCC5=CC=CC=C5)OC(=O)C

Technology Process of methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate

There total 16 articles about methyl (2R,3S,4S,5R,6R)-5-acetoxy-6-(((2R,3S,4R,5R,6S)-2-(acetoxymethyl)-4-(benzyloxy)-5-(((benzyloxy)carbonyl)amino)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)-4-(benzyloxy)-3-hydroxytetrahydro-2H-pyran-2-carboxylate 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: 85.0%

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-96-4) → methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-97-5)

Guidance literature:

With 2,6-dimethylpyridine; dithiocarbonic acid hydrazide; acetic acid; In methanol; dichloromethane; for 0.166667h;

DOI:10.1016/0008-6215(87)80268-9

Reference yield:

methyl 2--3-O-benzyl-2-deoxy-α-D-glucopyranoside (87907-35-5) → methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-97-5)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / CH₂Cl₂

2: 75 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

3: NaOMe; MeOH

4: CSA / acetone

5: DMAP; pyridine / CH₂Cl₂

6: aq. AcOH

7: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr

8: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol

With pyridine; methanol; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; acetic acid; potassium bromide; In dichloromethane; acetone; tert-butyl alcohol; 1: Acetylation / 2: Glycosidation / 3: Deacetylation / 4: Acetalization / 5: Acetylation / 6: Hydrolysis / 7: Oxidation / 8: Oxidation / 9: Esterification;

DOI:10.1016/S0960-894X(99)00550-8

Reference yield:

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside (114869-95-3) → methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (114869-97-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 75 percent / Sn(OTf)2 / CH₂Cl₂ / 0 °C

2: NaOMe; MeOH

3: CSA / acetone

4: DMAP; pyridine / CH₂Cl₂

5: aq. AcOH

6: 2,2,6,6-tetramethyl-1-piperidinyloxy radical; NaClO; KBr

7: NaClO₂; aq. NaH₂PO₄ / 2-methyl-propan-2-ol

With pyridine; methanol; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; acetic acid; potassium bromide; In dichloromethane; acetone; tert-butyl alcohol; 1: Glycosidation / 2: Deacetylation / 3: Acetalization / 4: Acetylation / 5: Hydrolysis / 6: Oxidation / 7: Oxidation / 8: Esterification;

DOI:10.1016/S0960-894X(99)00550-8

upstream raw materials:

methyl 6-O-acetyl-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-4-O-(methyl 2-O-acetyl-3-O-benzyl-4-O-chloroacetyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

methyl 6-O-acetyl-4-O-[2-O-acetyl-3-O-(phenylmethyl)-α-L-idopyranuronosyl)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-α-D-glucopyranoside

diazomethyl-trimethyl-silane

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

methyl(methyl 2-O-acetyl-3-O-benzyl-4-O-levulinoyl-α-L-idopyranosyluronate)-(1→4)-3-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

Refernces

• 1、 Petitou, Maurice,Duchaussoy, Philippe,Lederman, Isidore,Choay, Jean,Jaquinet, Jean-Claude,et al.. "SYNTHESIS OF HEPARIN FRAGMENTS: A METHYL α-PENTANOSIDE WITH HIGH AFFINITY FOR ANTITHROMBIN III". . p. 67 - 76. Retrieved 2007/10/02.