phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
CAS No.:340161-13-9
Molecular Formula:C₅₀H₅₂O₁₂S
Molecular Weight:877.022
Hs Code.:

Synonyms:phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

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Technology Process of phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

There total 7 articles about phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-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: 68.0%

: 340161-12-8
phenyl 2-O-acetyl-4,6-O-banelidene-1-thio-α-D-mannopyranoside

: 187226-47-7
O-(2-O-acetyl-3,4,6-tri-O-benzyl-α/β-D-mannopyranosyl)trichloroacetimidate

: 340161-13-9
phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -20 ℃; for 1h;
DOI:10.1016/j.tet.2005.05.098

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-Mannose pentaacetate

: 340161-13-9
phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 192.6 g / BF₃*Et₂O / CH₂Cl₂ / 20 °C

2.1: Na; MeOH / 20 °C

3.1: 57.7 percent / HBF₄ / CH₂Cl₂; diethyl ether / 20 °C

4.1: camphorsulfonic acid / 0.5 h / 20 °C

4.2: 75 percent / aq. AcOH / 1 h / 20 °C

5.1: 68 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -20 °C

With methanol; tetrafluoroboric acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium; In diethyl ether; dichloromethane; 4.1: Lemieux's acetylation;
DOI:10.1016/j.tet.2005.05.098

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 340161-13-9
phenyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 57.7 percent / HBF₄ / CH₂Cl₂; diethyl ether / 20 °C

2.1: camphorsulfonic acid / 0.5 h / 20 °C

2.2: 75 percent / aq. AcOH / 1 h / 20 °C

3.1: 68 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -20 °C

With tetrafluoroboric acid; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; In diethyl ether; dichloromethane; 2.1: Lemieux's acetylation;
DOI:10.1016/j.tet.2005.05.098