(2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

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Chemical Name:(2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside
CAS No.:220679-90-3
Molecular Formula:C₇₁H₉₂Cl₂O₁₉SSi
Molecular Weight:1380.56
Hs Code.:

(2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

Synonyms:(2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

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Chemical Property of (2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

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Technology Process of (2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

There total 19 articles about (2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside 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: 76.0%

: 220679-79-8
Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-1-thio-α-D-mannopyranoside

: 220679-89-0
(2'R,3'R) Phenyl 4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-1-seleno-β-D-galactopyranoside

: 220679-90-3
(2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With 4 A molecular sieve; methyl trifluoromethanesulfonate; In diethyl ether; toluene; at 20 ℃; for 1h;

Reference yield:

: 4981-97-9,23661-31-6,143995-76-0
phenyl 1-seleno-β-D-galactopyranoside

: 220679-90-3
(2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 67 percent / CSA / methanol / 16 h / Heating

2: 84 percent / imidazole / tetrahydrofuran / 5 h / 20 °C

3: 79 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: HF; H₂O / acetonitrile / 2 h / 20 °C

5: 71 percent / NIS; molecular sieves 4 Angstroem; TMSOTf / CH₂Cl₂; diethyl ether / 1 h / 20 °C

6: 76 percent / molecular sieves 4 Angstroem; MeOTf / toluene; diethyl ether / 1 h / 20 °C

With pyridine; 1H-imidazole; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; water; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 1: Etherification / 2: Etherification / 3: Acylation / 4: Desilylation / 5: Etherification / 6: Etherification;

Reference yield:

: 100-39-0
benzyl bromide

: 220679-90-3
(2'R,3'R) Ethyl 4-O-benzyl-6-O-tert-butyldimethylsilyl-2-O-chloroacetyl-3-O-(4-O-chloroacetyl-2,3-O-(2',3'-dimethoxybutane-2',3'-diyl)-6-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / dimethylformamide / 12 h / 20 °C

2: TBAF / tetrahydrofuran / 12 h / 20 °C

3: AcOH; H₂O / 6 h / 60 °C

4: imidazole / tetrahydrofuran / 2 h / 20 °C

5: NEt₃ / CH₂Cl₂ / 3 h / -78 - 20 °C

6: pyridine / CH₂Cl₂ / 1 h / -5 °C

7: HF; H₂O / acetonitrile / 0.5 h / 20 °C

8: 76 percent / molecular sieves 4 Angstroem; MeOTf / toluene; diethyl ether / 1 h / 20 °C

With pyridine; 1H-imidazole; 4 A molecular sieve; hydrogen fluoride; tetrabutyl ammonium fluoride; water; sodium hydride; acetic acid; triethylamine; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Etherification / 2: Desilylation / 3: Hydrolysis / 4: Etherification / 5: Etherification / 6: Acylation / 7: Desilylation / 8: Etherification;