methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

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Chemical Name:methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside
CAS No.:171076-03-2
Molecular Formula:C₁₈H₂₀O₅
Molecular Weight:316.354
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

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Technology Process of methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

There total 5 articles about methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside 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: 90.0%

: 171076-02-1
methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-3-C-propanone-α-D-erythro-hexopyranosid-2-ulose

: 171076-03-2
methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

Guidance literature:: With potassium tert-butylate; In toluene; for 0.5h;
DOI:10.1039/c39950001567

Reference yield:

: 131529-45-8
methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-enyl)-α-D-altropyranoside

: 171076-03-2
methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) trifluoroacetic anhydride, dimethyl sulfoxide, 2.) triethylamine / 1.) CH₂Cl₂, -65 deg C, 1.5 h, 2.) CH₂Cl₂, 24 h

2: 1.) lithium hexamethyldisilazide, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 0 deg C, 1 h, 2.) THF, room temperature, 24 h

3: 56 percent / palladium(II) chloride, copper(II) chloride, oxygen / dimethylformamide; H₂O / Ambient temperature

4: 90 percent / potassium tert-butoxide / toluene / 0.5 h / Ambient temperature

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium tert-butylate; oxygen; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; copper dichloride; palladium dichloride; lithium hexamethyldisilazane; In water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo981225j

Reference yield:

: 135700-48-0
methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

: 171076-03-2
methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-methyl-3,2-C-(2'-oxapropan-1'-yl-3'-ylidene)-α-D-arabino-hexopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) lithium hexamethyldisilazide, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, 0 deg C, 1 h, 2.) THF, room temperature, 24 h

2: 56 percent / palladium(II) chloride, copper(II) chloride, oxygen / dimethylformamide; H₂O / Ambient temperature

3: 90 percent / potassium tert-butoxide / toluene / 0.5 h / Ambient temperature

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium tert-butylate; oxygen; copper dichloride; palladium dichloride; lithium hexamethyldisilazane; In water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo981225j