(4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane

Base Information

• Chemical Name: (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane
• CAS No.: 172794-66-0
• Molecular Formula: C₁₄H₁₉BrO₄
• Molecular Weight: 331.206
• Mol file: 172794-66-0.mol

Synonyms:(4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane

Chemical Property of (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane

There total 2 articles about (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane 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: 88.3%

(-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol (50622-10-1) + 2-(2-bromophenyl)acetaldehyde dimethyl acetal (112396-13-1) → (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane (172794-66-0)

Guidance literature:

With 4 A molecular sieve; toluene-4-sulfonic acid; In tetrahydrofuran; for 72h; Heating;

DOI:10.1002/(SICI)1099-0690(199804)1998:4<711::AID-EJOC711>3.0.CO;2-A

Reference yield: 85.7%

(-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol (50622-10-1) + 1-bromo-2-(2-methoxyethenyl)benzene (130089-19-9,130089-23-5,59436-11-2) → (4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane (172794-66-0)

Guidance literature:

With 4 A molecular sieve; toluene-4-sulfonic acid; In tetrahydrofuran; for 72h; Heating;

DOI:10.1002/(SICI)1099-0690(199804)1998:4<711::AID-EJOC711>3.0.CO;2-A

Reference yield:

(4S,5S)-2-(2-Bromo-benzyl)-4,5-bis-methoxymethyl-[1,3]dioxolane (172794-66-0) → (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8,96719-89-0,118864-75-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) -105 deg C

2: p-toluenesulfonic acid / methanol / Heating

3: H₂ / Pd/C

With n-butyllithium; hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol;

DOI:10.1016/0040-4039(95)01716-U

upstream raw materials:

(-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol

2-(2-bromophenyl)acetaldehyde dimethyl acetal

1-bromo-2-(2-methoxyethenyl)benzene

Downstream raw materials:

(-)-(2S,3S)-1,4-dimethoxy-2,3-butanediol

(R)-(+)-benzyl 1-phenyl-1,2-dihydroisoquinoline-2-carboxylate

(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline

(S)-(-)-benzyl 1-phenyl-1,2-dihydroisoquinoline-2-carboxylate