methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside
• CAS No.: 652991-32-7
• Molecular Formula: C₅₄H₆₆O₁₀Si
• Molecular Weight: 903.198

Synonyms:

Chemical Property of methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

There total 8 articles about methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-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:

methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1,3-dideoxy-D-ribo-hept-2-enitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside (652991-31-6) → methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside (652991-32-7) + methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-allo-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

Guidance literature:

methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1,3-dideoxy-D-ribo-hept-2-enitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside; With dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃;

With sodium hydroxide; dihydrogen peroxide; In water; at 0 ℃; for 0.5h;

DOI:10.1081/CAR-120026467

Reference yield:

methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanoic acid)-α-D-glucopyranoside (224324-88-3) → methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside (652991-32-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / DCC; DMAP / benzene / 0 - 20 °C

2.1: 60 percent / pyridine / tetrahydrofuran; toluene / -78 - 20 °C

3.1: 2,6-di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.25 h / 20 °C

3.2: 70 percent / methyl triflate / CH₂Cl₂ / 0 - 20 °C

4.1: BH₃*SMe₂ / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

4.2: NaOH; H₂O₂ / H₂O / 0.5 h / 0 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; dimethylsulfide borane complex; 4 A molecular sieve; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; toluene; benzene;

DOI:10.1081/CAR-120026467

Reference yield:

1-O-acetyl-4-O-tert-butyl(diphenyl)silyl-3-O-formyl-1,2-O-isopropylidene-D-erythro-hemiacetal → methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside (652991-32-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / -78 - -40 °C

2.1: NaOMe / methanol / 0.5 h / 20 °C

3.1: 85 percent / DCC; DMAP / benzene / 0 - 20 °C

4.1: 60 percent / pyridine / tetrahydrofuran; toluene / -78 - 20 °C

5.1: 2,6-di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.25 h / 20 °C

5.2: 70 percent / methyl triflate / CH₂Cl₂ / 0 - 20 °C

6.1: BH₃*SMe₂ / CH₂Cl₂; tetrahydrofuran / 0 - 20 °C

6.2: NaOH; H₂O₂ / H₂O / 0.5 h / 0 °C

With pyridine; dmap; 2,6-di-tert-butyl-4-methylpyridine; dimethylsulfide borane complex; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1081/CAR-120026467

upstream raw materials:

methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1,3-dideoxy-D-ribo-hept-2-enitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanoic acid)-α-D-glucopyranoside

4-O-tert-butyl(diphenyl)silyl-1,2-O-isopropylidene-D-erythro-S-phenyl monothiohemiacetal

((2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl)-acetic acid (R)-2-(tert-butyl-diphenyl-silanyloxy)-1-((R)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethyl ester

Downstream raw materials:

methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

methyl 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside

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