allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Base Information

Chemical Name:allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside
CAS No.:139525-90-9
Molecular Formula:C₅₄H₅₇NO₁₂
Molecular Weight:912.046
Hs Code.:

Synonyms:allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

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Chemical Property of allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

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Technology Process of allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

There total 16 articles about allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 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:

: 85-44-9
phthalic anhydride

: (2R,3R,4R,5R,6R)-2-Allyloxy-5-benzyloxy-4-((3aS,4R,6R,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-3-ylamine

: 139525-90-9
allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Guidance literature:: With triethylamine; In 1,2-dichloro-ethane; at 50 ℃; for 18h; Yield given;
DOI:10.1021/jo00032a601

Reference yield:

: 100-39-0
benzyl bromide

: 139525-90-9
allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: NaH / dimethylformamide / 1) 0 deg C, 1h, 2) RT, 2h

2: DDQ / CH₂Cl₂; H₂O / 1) 0 deg C, 0.5h, 2) RT, 2h

3: 91 percent / MeOSO₂CF₃, molecular sieve 4A / CCl₄; toluene / 8 h / 50 °C

4: 1M NaOMe / methanol; CH₂Cl₂ / 3 h / Heating

5: imidazole / dimethylformamide / 1) 0 deg C, 1.5h, 2) RT, 0.5h

6: (+/-)-10-camphorsulfonic acid / acetonitrile / 18 h / Ambient temperature

7: Bu₄NF / tetrahydrofuran / 1) 0 deg C, 1.5h, 2) RT, 1h

8: 97 percent / NaH / dimethylformamide / 1) 0 deg C, 1h, 2) RT, 2h

9: LiAlH₄ / diethyl ether / 2 h / -40 deg C to RT

10: Et₃N / 1,2-dichloro-ethane / 18 h / 50 °C

With 1H-imidazole; lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00032a601

Reference yield:

: 90405-24-6
allyl 2-deoxy-2-azido-4,6-benzylidene-β-D-galactopyranoside

: 139525-90-9
allyl O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-4,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1: NaH / dimethylformamide / 1) 0 deg C, 0.5h, 2) RT, 1h

2: (+/-)-10-camphorsulfonic acid / toluene; methanol / 18 h / Ambient temperature

3: NaH / dimethylformamide / 1) 0 deg C, 1h, 2) RT, 2h

4: DDQ / CH₂Cl₂; H₂O / 1) 0 deg C, 0.5h, 2) RT, 2h

5: 91 percent / MeOSO₂CF₃, molecular sieve 4A / CCl₄; toluene / 8 h / 50 °C

6: 1M NaOMe / methanol; CH₂Cl₂ / 3 h / Heating

7: imidazole / dimethylformamide / 1) 0 deg C, 1.5h, 2) RT, 0.5h

8: (+/-)-10-camphorsulfonic acid / acetonitrile / 18 h / Ambient temperature

9: Bu₄NF / tetrahydrofuran / 1) 0 deg C, 1.5h, 2) RT, 1h

10: 97 percent / NaH / dimethylformamide / 1) 0 deg C, 1h, 2) RT, 2h

11: LiAlH₄ / diethyl ether / 2 h / -40 deg C to RT

12: Et₃N / 1,2-dichloro-ethane / 18 h / 50 °C

With 1H-imidazole; lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00032a601