(S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester

Base Information

• Chemical Name: (S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester
• CAS No.: 324530-42-9
• Molecular Formula: C₆₁H₆₃N₃O₁₄
• Molecular Weight: 1062.18
• Mol file: 324530-42-9.mol

Synonyms:

Chemical Property of (S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester

There total 8 articles about (S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl 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: 27.0%

(S)-2-((S)-2-{(R)-3-Benzyloxy-2-[((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-propionylamino}-3-carboxy-propionylamino)-pentanedioic acid dibenzyl ester (324530-41-8) → (S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester (324530-42-9)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 12h;

DOI:10.1016/S0040-4039(00)01653-1

Reference yield:

Methyl-D-galactopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3149-68-6,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6) → (S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester (324530-42-9)

Guidance literature:

Multi-step reaction with 9 steps

1: NaH; Bu₄NI / 4 h

2: 71 percent / TMSOTf / acetonitrile / 12 h

3: pyridine / 2 h

4: O₃; Me₂S / 8 h

5: CrO₃; aq. H₂SO₄ / acetone / 0.5 h

6: NaOMe / methanol / 1 h

7: EDC; HOBt; NMM / 2 h

8: Rh(PPh₃)3Cl / ethanol; H₂O / 2 h

9: 27 percent / PPh₃; DEAD / tetrahydrofuran / 12 h

With 4-methyl-morpholine; pyridine; chromium(VI) oxide; Wilkinson's catalyst; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; water; acetone; acetonitrile; 5: Jones oxidation / 9: Mitsunobu reaction;

DOI:10.1016/S0040-4039(00)01653-1

Reference yield:

2,3,4,6-Tetra-O-benzyl-methyl-α/β-D-galactopyranoside (324530-37-2) → (S)-2-[((1R,4R,7S,12S,13R,14R,15S)-13,14,15-Tris-benzyloxy-4-benzyloxymethyl-2,5,9-trioxo-10,16-dioxa-3,6-diaza-bicyclo[10.3.1]hexadecane-7-carbonyl)-amino]-pentanedioic acid dibenzyl ester (324530-42-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / TMSOTf / acetonitrile / 12 h

2: pyridine / 2 h

3: O₃; Me₂S / 8 h

4: CrO₃; aq. H₂SO₄ / acetone / 0.5 h

5: NaOMe / methanol / 1 h

6: EDC; HOBt; NMM / 2 h

7: Rh(PPh₃)3Cl / ethanol; H₂O / 2 h

8: 27 percent / PPh₃; DEAD / tetrahydrofuran / 12 h

With 4-methyl-morpholine; pyridine; chromium(VI) oxide; Wilkinson's catalyst; dimethylsulfide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium methylate; benzotriazol-1-ol; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; ethanol; water; acetone; acetonitrile; 4: Jones oxidation / 8: Mitsunobu reaction;

DOI:10.1016/S0040-4039(00)01653-1

upstream raw materials:

(S)-2-((S)-2-{(R)-3-Benzyloxy-2-[((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-propionylamino}-3-carboxy-propionylamino)-pentanedioic acid dibenzyl ester

Methyl-D-galactopyranoside

2,3,4,6-Tetra-O-benzyl-methyl-α/β-D-galactopyranoside

((2S,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-propa-1,2-dienyl-tetrahydro-pyran-2-yl)-methanol