methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside
CAS No.:131289-44-6
Molecular Formula:C₂₁H₃₄O₈Si
Molecular Weight:442.582
Hs Code.:

Synonyms:methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

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Technology Process of methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

There total 5 articles about methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside 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: 82.0%

: 131289-43-5
methyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

: 131289-44-6
methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; for 24h; under 3000.2 Torr;
DOI:10.1016/0008-6215(90)80133-N

Reference yield:

: 40653-15-4
methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

: 131289-44-6
methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 1) magnesium, dibromoethane / 1) THF, reflux, 2) 2 h, 0 deg C

2: 3.7 g / 30percent H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 15 h / Heating

3: pyridine / 0 deg C to r. t., overnight

4: 0.41 g / pyridine, 4-dimethylaminopyridine / 0.5 h

5: 82 percent / H₂ / 10percent Pd-C / ethyl acetate / 24 h / 3000.2 Torr

With pyridine; dmap; 1,1-Dibromoethane; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; magnesium; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate;
DOI:10.1016/0008-6215(90)80133-N

Reference yield:

: 127588-70-9
(R)-2-(Isopropoxy-dimethyl-silanyl)-1-((2R,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-ethanol

: 131289-44-6
methyl 6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 3.7 g / 30percent H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 15 h / Heating

2: pyridine / 0 deg C to r. t., overnight

3: 0.41 g / pyridine, 4-dimethylaminopyridine / 0.5 h

4: 82 percent / H₂ / 10percent Pd-C / ethyl acetate / 24 h / 3000.2 Torr

With pyridine; dmap; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate;
DOI:10.1016/0008-6215(90)80133-N