methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 131444-89-8
• Molecular Formula: C₄₃H₅₄O₁₃
• Molecular Weight: 778.894
• Mol file: 131444-89-8.mol

Synonyms:methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

There total 25 articles about methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 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: 76.0%

methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (271245-12-6) → methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (131444-89-8)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 90 ℃; for 2h;

DOI:10.1016/S0957-4166(99)00557-1

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (131444-89-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 71 percent / n-BuLi / tetrahydrofuran; hexane / 15 h / 20 °C

2: 88 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 40 °C

3: 1) BH₃/THF, 2) 25percent H₂O₂, NaOH / 1) THF, 0 deg C to rt, 30 min, 2) THF, H₂O

4: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1.5 h / Ambient temperature

5: 67 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 67 percent / pyridine / toluene / 1) -45 deg C, 1 h, 2) 0 deg C, 30 min

7: 80 percent / Bu₄NF, ethylenediamine / tetrahydrofuran; hexamethylphosphoric acid triamide / 18 h / 60 °C

8: 1) t-BuOK, 2) I₂ / 1) THF, rt, 10 min, 2) -78 deg C to rt, 4 h

9: 68 percent / hexamethylphosphoric acid triamide / 24 h / 130 °C

10: 98 percent / NaOCH₃ / methanol / 1 h / Ambient temperature

11: 1) (COCl)2, 2) NaClO₂, H₂O₂ / 1) CH₂Cl₂, DMSO, 2) CH₃CN, H₂O, rt, 3 h

12: diethyl ether

With tetrahydrofuran; pyridine; dmap; ruthenium trichloride; sodium hydroxide; sodium chlorite; sodium periodate; n-butyllithium; oxalyl dichloride; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; sodium methylate; ethylenediamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo00041a017

Reference yield:

2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptitol (137945-80-3) → methyl O-(methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside (131444-89-8)

Guidance literature:

Multi-step reaction with 9 steps

1: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

2: 78 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 81 percent / pyridine / toluene / 1) -45 deg C, 1 h, 2) 0 deg C, 30 min

4: 93 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

5: 1) t-BuOK, 2) I₂ / 1) THF, rt, 10 min, 2) -78 deg C to rt, 4 h

6: 68 percent / hexamethylphosphoric acid triamide / 24 h / 130 °C

7: 98 percent / NaOCH₃ / methanol / 1 h / Ambient temperature

8: 1) (COCl)2, 2) NaClO₂, H₂O₂ / 1) CH₂Cl₂, DMSO, 2) CH₃CN, H₂O, rt, 3 h

9: diethyl ether

With pyridine; dmap; ruthenium trichloride; sodium chlorite; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; potassium tert-butylate; dihydrogen peroxide; iodine; sodium methylate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; tetrachloromethane; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo00041a017

upstream raw materials:

diazomethane

methyl O-(methyl 4,5:7,8-di-O-isopropylidene-3-O-thiobenzoyl-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl O-(methyl 4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl O-(methyl 3-O-benzoyl-4,5:7,8-di-O-isopropylidene-α-D-glycero-D-talo-2-octulopyranosonate)-(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

methyl (methyl 3-deoxy-α-D-manno-octulosonate)-(2->6)-(2,3,4-tri-O-benzyl-α-D-glucopyranoside)