Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester
• CAS No.: 156487-70-6
• Molecular Formula: C₁₈H₂₅BrO₈
• Molecular Weight: 449.296

Synonyms:Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester

There total 2 articles about Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester 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: 90.0%

Methyl 4,6-O-benzylidene-2,3-bis-O-(methoxymethyl)-α-D-altropyranoside (156487-69-3) → Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester (156487-70-6)

Guidance literature:

With N-Bromosuccinimide; barium carbonate; In tetrachloromethane; for 20h; Heating;

DOI:10.1039/a604365h

Reference yield:

methyl 4,6-O-benzylidene-α-D-altropyranoside (71117-41-4) → Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester (156487-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-diisopropylethylamine / CH₂Cl₂ / 18 h / Heating

2: 90 percent / NBS, BaCO₃ / CCl₄; various solvent(s) / 20 h / Heating

With N-Bromosuccinimide; N-ethyl-N,N-diisopropylamine; barium carbonate; In tetrachloromethane; dichloromethane;

DOI:10.1039/a604365h

Reference yield: 96.0%

Benzoic acid (2S,3S,4R,5S,6S)-2-bromomethyl-6-methoxy-4,5-bis-methoxymethoxy-tetrahydro-pyran-3-yl ester (156487-70-6) → Benzoic acid (3S,4R,5S,6S)-6-methoxy-4,5-bis-methoxymethoxy-2-methylene-tetrahydro-pyran-3-yl ester (156487-71-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 75 ℃; for 20h;

DOI:10.1039/a604365h

upstream raw materials:

Methyl 4,6-O-benzylidene-2,3-bis-O-(methoxymethyl)-α-D-altropyranoside

methyl 4,6-O-benzylidene-α-D-altropyranoside

Downstream raw materials:

Benzoic acid (3S,4R,5S,6S)-6-methoxy-4,5-bis-methoxymethoxy-2-methylene-tetrahydro-pyran-3-yl ester

(3R,4R)-3,4-Bis(methoxymethoxy)-1-(3,4-dimethoxyphenyl)-cyclohexene

1L-<1(OH),2,3/4>-3,4-Bis-O-(methoxymethyl)-1-(3,4-dimethoxyphenyl)cyclohexane-1,2,3,4-tetrol

1L-<1(OH),2,3/4>-3,4-Bis-O-(methoxymethyl)-1-(3,4-dimethoxyphenyl)cyclohex-5-ene-1,2,3,4-tetrol

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