Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Base Information

Chemical Name:Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside
CAS No.:171356-78-8
Molecular Formula:C₅₄H₆₆O₁₁Si
Molecular Weight:919.197
Hs Code.:

Synonyms:Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

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Chemical Property of Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

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Technology Process of Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

There total 8 articles about Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside 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: 59.0%

: 67-56-1
methanol

: [(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane

: 171356-78-8
Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

: [(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-3-((2R,4aR,6R,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-methoxy-tetrahydro-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; iodosylbenzene; 4 A molecular sieve; In dichloromethane; at -15 ℃; for 1h;
DOI:10.1055/s-1999-2997

Reference yield:

: 22352-19-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate

: 171356-78-8
Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / ZnI₂ / CH₂Cl₂ / 20 °C

2: NaOMe / methanol / 4 h / 20 °C

3: TsOH*2H₂O / dimethylformamide / 3 h / 60 °C / 15 Torr

4: pyridine; DMAP / dimethylformamide / 20 °C

5: NaH / dimethylformamide / 20 °C

6: 36 percent / PhIO; TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -15 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; iodosylbenzene; 4 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; zinc(II) iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Deacetylation / 3: Etherification / 4: Etherification / 5: Etherification / 6: Etherification;
DOI:10.1055/s-1999-2997

Reference yield:

: 5346-81-6,28022-13-1,28022-14-2
phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

: 171356-78-8
Methyl O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranosyl)-(1->4)-2,3-di-O-benzyl-6-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: NaOMe / methanol / 4 h / 20 °C

2: TsOH*2H₂O / dimethylformamide / 3 h / 60 °C / 15 Torr

3: pyridine; DMAP / dimethylformamide / 20 °C

4: NaH / dimethylformamide / 20 °C

5: 36 percent / PhIO; TMSOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -15 °C

With pyridine; dmap; trimethylsilyl trifluoromethanesulfonate; iodosylbenzene; 4 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: Deacetylation / 2: Etherification / 3: Etherification / 4: Etherification / 5: Etherification;
DOI:10.1055/s-1999-2997