allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside

Base Information

Chemical Name:allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside
CAS No.:727991-24-4
Molecular Formula:C₃₈H₅₁NO₁₄Si
Molecular Weight:773.907
Hs Code.:

Synonyms:allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside

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Chemical Property of allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside

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Technology Process of allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside

There total 11 articles about allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-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: 62.0%

: 727991-23-3
allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-4,6-O-p-methoxybenzylidene-2-deoxy-2-acetamido-β-D-galactopyranoside

: 727991-24-4
allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 3h;
DOI:10.1021/ja0484045

Reference yield:

: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-galactopyranoside

: 727991-24-4
allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 0.044 g / BF₃*Et₂O / CH₂Cl₂ / 3 h / 20 °C

2: NaOMe / CH₂Cl₂; methanol / 2 h / 20 °C

3: 13 g / DL-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

4: 75 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 16 h

5: 79 percent / N-iodosuccinimide; triflic acid; 4A molecular sieves / CH₂Cl₂ / 0.17 h / 0 °C

6: 85 percent / Bu₄NF / tetrahydrofuran / 20 h / 20 °C

7: 74 percent / 4A molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -40 - -10 °C

8: 85 percent / tributylstannane; 2,2'-azobisisobutyronitrile / benzene / 2.25 h / 20 - 80 °C

9: 62 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 3 h / 20 °C

With 1H-imidazole; dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; sodium methylate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja0484045

Reference yield:

: 727991-13-1
p-tolyl 2-deoxy-2-trichloracetamido-1-thio-β-D-galactopyranoside

: 727991-24-4
allyl (methyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-glucopyranosyluronate)-(1->3)-2-deoxy-2-acetamido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 13 g / DL-10-camphorsulfonic acid / acetonitrile / 12 h / 20 °C

2: 75 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 16 h

3: 79 percent / N-iodosuccinimide; triflic acid; 4A molecular sieves / CH₂Cl₂ / 0.17 h / 0 °C

4: 85 percent / Bu₄NF / tetrahydrofuran / 20 h / 20 °C

5: 74 percent / 4A molecular sieves; trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -40 - -10 °C

6: 85 percent / tributylstannane; 2,2'-azobisisobutyronitrile / benzene / 2.25 h / 20 - 80 °C

7: 62 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 3 h / 20 °C

With 1H-imidazole; dmap; N-iodo-succinimide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/ja0484045