(1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside

Base Information

Chemical Name:(1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside
CAS No.:217971-16-9
Molecular Formula:C₃₄H₄₀Br₂O₁₀
Molecular Weight:768.494
Hs Code.:

Synonyms:(1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside

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Chemical Property of (1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside

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Technology Process of (1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside

There total 5 articles about (1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-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: 31.0%

: 15356-60-2
(1S,2R,5S)-(+)-menthol

: 217970-64-4
2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-α-D-galactopyranosyl bromide

: 217971-16-9
(1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at -40 ℃;
DOI:10.1021/jo981002t

Reference yield:

: 3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0
4,6-O-benzylidene-α,β-D-galactopyranose

: 217971-16-9
(1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / pyridine / 20 °C

2: 89 percent / AcOH; H₂O / 60 °C

3: 80 percent / pyridine; DMAP / 60 °C

4: 71 percent / HBr; AcOH / CH₂Cl₂

5: 31 percent / 1,1,3,3-tetramethylurea; silver trifluoromethanesulfonate / CH₂Cl₂ / -40 °C

With pyridine; dmap; water; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; tetramethylurea; In dichloromethane; 1: Acetylation / 2: Hydrolysis / 3: Acylation / 4: Substitution / 5: Substitution;
DOI:10.1021/jo981002t

Reference yield:

: 243136-79-0
4,6-O-benzylidene-1,2,3-tris-O-acetyl-D-galactopyranoside

: 217971-16-9
(1S,2R,5S)-(+)-1-menthyl 2,3-bis-O-acetyl-4,6-bis-O-(p-bromobenzoyl)-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / AcOH; H₂O / 60 °C

2: 80 percent / pyridine; DMAP / 60 °C

3: 71 percent / HBr; AcOH / CH₂Cl₂

4: 31 percent / 1,1,3,3-tetramethylurea; silver trifluoromethanesulfonate / CH₂Cl₂ / -40 °C

With pyridine; dmap; water; hydrogen bromide; silver trifluoromethanesulfonate; acetic acid; tetramethylurea; In dichloromethane; 1: Hydrolysis / 2: Acylation / 3: Substitution / 4: Substitution;
DOI:10.1021/jo981002t