methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside

Base Information

Chemical Name:methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside
CAS No.:753491-01-9
Molecular Formula:C₂₀H₃₂O₉S
Molecular Weight:448.535
Hs Code.:

Synonyms:methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside

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Chemical Property of methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside

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Technology Process of methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside

There total 7 articles about methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside 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:

: 83075-53-0,89177-22-0,129454-52-0,51433-19-3
methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranoside

: 753491-01-9
methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

2: TiCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

3: NaH / dimethylformamide / 0.75 h / 20 °C

4: ozone / methanol; CH₂Cl₂ / -78 °C

5: NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

6: 901 mg / pyridine / 1.5 h

With pyridine; sodium tetrahydroborate; titanium tetrachloride; sodium hydride; Dess-Martin periodane; ozone; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Dess-Martin oxidation / 2: Sakurai alkylation;
DOI:10.1021/ja047578j

Reference yield:

: 3013-58-9,3051-89-6,4261-46-5,6748-99-8,13035-20-6,13502-46-0,22893-88-5,35311-32-1,53767-28-5,56586-53-9,56586-54-0,69744-11-2,94480-09-8,120200-48-8,120200-49-9,120200-50-2,120200-52-4
methyl 4,6-O-benzylidene-2,3-di-O-methyl-α,D-glucopyranoside

: 753491-01-9
methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / BH₃*THF; Sc(OTf)3 / CH₂Cl₂ / 6 h

2: Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / 20 °C

3: TiCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

4: NaH / dimethylformamide / 0.75 h / 20 °C

5: ozone / methanol; CH₂Cl₂ / -78 °C

6: NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

7: 901 mg / pyridine / 1.5 h

With pyridine; sodium tetrahydroborate; borane-THF; titanium tetrachloride; sodium hydride; Dess-Martin periodane; ozone; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; N,N-dimethyl-formamide; 2: Dess-Martin oxidation / 3: Sakurai alkylation;
DOI:10.1021/ja047578j

Reference yield:

: (2S,3S,4S,5R,6S)-3-Benzyloxy-4,5,6-trimethoxy-tetrahydro-pyran-2-carbaldehyde

: 753491-01-9
methyl 4-O-benzyl-7-deoxy-2,3,6-tri-O-methyl-8-O-methylsulfonyl-β-L-glycero-D-glucooctopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: TiCl₄ / CH₂Cl₂ / 2.5 h / -78 °C

2: NaH / dimethylformamide / 0.75 h / 20 °C

3: ozone / methanol; CH₂Cl₂ / -78 °C

4: NaBH₄ / methanol; CH₂Cl₂ / -78 - 20 °C

5: 901 mg / pyridine / 1.5 h

With pyridine; sodium tetrahydroborate; titanium tetrachloride; sodium hydride; ozone; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Sakurai alkylation;
DOI:10.1021/ja047578j