{(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid

Base Information

• Chemical Name: {(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid
• CAS No.: 207387-07-3
• Molecular Formula: C₅₁H₅₅NO₁₃
• Molecular Weight: 889.997
• Mol file: 207387-07-3.mol

Synonyms:{(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid

Chemical Property of {(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid

There total 12 articles about {(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic 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:

(2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carboxylic acid [(2S,4aR,6R,7S,8R,8aR)-6-methoxy-8-(2-oxo-ethoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-amide → {(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid (207387-07-3)

Guidance literature:

With jones reagent; In acetone; at 0 ℃; Yield given;

DOI:10.1021/ja970920q

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → {(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid (207387-07-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / CSA / acetonitrile / 0.5 h

2: 1.) Bu₂SnO, 2.) TBAI / 1.) toluene, 130 deg C, 2 h, 2.) 130 deg C, 24 h

3: 1.) (COCl)2, DMSO, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) -78 deg C -> 23 deg c

4: NH₄OAc, NaBH₃CN / methanol / 48 h

5: 63 percent / HOBt, NMM, EDC / CH₂Cl₂ / 1.) 0 deg C -> 23 deg C, 2.) 23 deg C, 24 h

6: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, -78 deg C, 2.) 23 deg C, 4 h

7: Jones reagent / acetone / 0 °C

With 4-methyl-morpholine; jones reagent; oxalyl dichloride; 2,3-dimercapto-succinic acid; camphor-10-sulfonic acid; ammonium acetate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; sodium cyanoborohydride; benzotriazol-1-ol; ozone; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; acetone; acetonitrile;

DOI:10.1021/ja970920q

Reference yield:

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene (82659-59-4) → {(2S,4aR,6R,7S,8R,8aR)-6-Methoxy-2-phenyl-7-[((2S,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid (207387-07-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 46 percent / PdCl₂ / benzene / 24 h / Heating

2: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, -78 deg C, 2.) 23 deg C, 24 h

3: 634 mg / Jones reagent / acetone / 0 °C

4: 63 percent / HOBt, NMM, EDC / CH₂Cl₂ / 1.) 0 deg C -> 23 deg C, 2.) 23 deg C, 24 h

5: 1.) O₃, 2.) DMS / 1.) CH₂Cl₂, -78 deg C, 2.) 23 deg C, 4 h

6: Jones reagent / acetone / 0 °C

With 4-methyl-morpholine; jones reagent; 2,3-dimercapto-succinic acid; benzotriazol-1-ol; ozone; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium dichloride; In dichloromethane; acetone; benzene;

DOI:10.1021/ja970920q

upstream raw materials:

benzaldehyde dimethyl acetal

3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)propene

(2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde

Methyl 3-O-allyl-4,6-O-benzylidene-β-D-galactopyranoside