allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside
CAS No.:134136-26-8
Molecular Formula:C₅₁H₅₃NO₁₁
Molecular Weight:855.982
Hs Code.:

Synonyms:allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

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Technology Process of allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

There total 9 articles about allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside 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%

: 134136-24-6
allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

: 134136-26-8
allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With methanol; acetyl chloride; for 4h; Ambient temperature;
DOI:10.1016/0008-6215(91)80123-5

Reference yield:

: 100-39-0
benzyl bromide

: 134136-26-8
allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaH / 1) THF, 15 min, 2) THF, 36 h, r. t.

2: Rh(PPh₃)3Cl / ethanol; H₂O / 18 h / Heating

3: HgO(yellow), HgCl₂ / acetone; H₂O / 18 h

4: 97 percent / oxalyl chloride, DMF / CH₂Cl₂ / 2 h / 0 °C

5: 61 percent / CF₃SO₃Ag, collidine, 4 Angstroem molecular sieves / CH₂Cl₂ / 36 h / Ambient temperature

6: 90 percent / AcCl, MeOH / 4 h / Ambient temperature

With 2,3,5-trimethyl-pyridine; methanol; oxalyl dichloride; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; acetyl chloride; N,N-dimethyl-formamide; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In ethanol; dichloromethane; water; acetone;
DOI:10.1016/0008-6215(91)80123-5

Reference yield:

: 114853-29-1
allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

: 134136-26-8
allyl 3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 1) NaH / 1) THF, 15 min, 2) THF, 36 h, r. t.

2: Rh(PPh₃)3Cl / ethanol; H₂O / 18 h / Heating

3: HgO(yellow), HgCl₂ / acetone; H₂O / 18 h

4: 97 percent / oxalyl chloride, DMF / CH₂Cl₂ / 2 h / 0 °C

5: 61 percent / CF₃SO₃Ag, collidine, 4 Angstroem molecular sieves / CH₂Cl₂ / 36 h / Ambient temperature

6: 90 percent / AcCl, MeOH / 4 h / Ambient temperature

With 2,3,5-trimethyl-pyridine; methanol; oxalyl dichloride; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; acetyl chloride; N,N-dimethyl-formamide; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In ethanol; dichloromethane; water; acetone;
DOI:10.1016/0008-6215(91)80123-5