(1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol

Base Information

• Chemical Name: (1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol
• CAS No.: 85716-47-8
• Molecular Formula: C₂₈H₂₈Br₂O₃
• Molecular Weight: 572.337
• Mol file: 85716-47-8.mol

Synonyms:(1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol

Chemical Property of (1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol

There total 7 articles about (1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol 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: 84.0%

1D-(1,3/2)-1,2,3-tri-O-benzyl-4-methylene-5-cyclohexen-1,2,3-triol (85716-46-7) → (1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol (85716-47-8)

Guidance literature:

With bromine; In dichloromethane;

DOI:10.1016/S0040-4039(00)85830-X

Reference yield:

1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon (85716-45-6) → (1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol (85716-47-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / mesyl chloride / pyridine

2: 77 percent / diethyl ether / Ambient temperature

3: 84 percent / Br₂ / CH₂Cl₂

With bromine; methanesulfonyl chloride; In pyridine; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)85830-X

Reference yield:

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one (85798-11-4) → (1R,2R,3S,4R)-1,2,3-tri-O-benzyl-6-bromo-4-(bromomethyl)-4-cyclohexene-1,2,3-triol (85716-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / diethyl ether / Ambient temperature

2: 84 percent / Br₂ / CH₂Cl₂

With bromine; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)85830-X

upstream raw materials:

1D-(1,3/2)-1,2,3-tri-O-benzyl-4-methylene-5-cyclohexen-1,2,3-triol

1L-(2,4,5/3)-2,3,4-Tri-O-benzyl-2,3,4,5-tetrahydroxy-1-cyclohexanon

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one

Methanesulfonic acid (2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

(1R,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(trityloxymethyl)-5-cyclohexene-1,2,3,4-tetrol

(1S,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(trityloxymethyl)-5-cyclohexene-1,2,3,4-tetrol

(1R,2S,3S,4R)-1-phthalimido-2,3,4-tri-O-benzyl-5-(hydroxymethyl)-5-cyclohexene-2,3,4-triol

(1S,2S,3S,4R)-1-phthalimido-2,3,4-tri-O-benzyl-5-(hydroxymethyl)-5-cyclohexene-2,3,4-triol