Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 87357-68-4
• Molecular Formula: C₇₇H₁₀₈N₂O₁₇
• Molecular Weight: 1333.71
• Mol file: 87357-68-4.mol

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester

There total 5 articles about Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-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:

(R)-3-hydroxytetradecanoic acid (28715-21-1,3422-31-9) → Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester (87357-68-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / Et₃N / ethyl acetate

2: Ag₂O / benzene / 48 h / Ambient temperature

3: Zn-powder / acetic acid / 3 h / 50 °C

4: dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃

With triethylamine; dicyclohexyl-carbodiimide; silver(l) oxide; zinc; In tetrahydrofuran; chloroform; acetic acid; ethyl acetate; benzene;

DOI:10.1016/S0040-4039(00)81830-4

Reference yield:

benzyl bromide (100-39-0) → Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester (87357-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Ag₂O / benzene / 48 h / Ambient temperature

2: Zn-powder / acetic acid / 3 h / 50 °C

3: dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃

With dicyclohexyl-carbodiimide; silver(l) oxide; zinc; In tetrahydrofuran; chloroform; acetic acid; benzene;

DOI:10.1016/S0040-4039(00)81830-4

Reference yield:

(3R)-3-hydroxytetradecanoic acid phenacyl ester (87357-65-1) → Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-[(2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-3-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-2-yloxymethyl]-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-tetrahydro-pyran-4-yl ester (87357-68-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Ag₂O / benzene / 48 h / Ambient temperature

2: Zn-powder / acetic acid / 3 h / 50 °C

3: dicyclohexylcarbodiimide / tetrahydrofuran; CHCl₃

With dicyclohexyl-carbodiimide; silver(l) oxide; zinc; In tetrahydrofuran; chloroform; acetic acid; benzene;

DOI:10.1016/S0040-4039(00)81830-4

upstream raw materials:

(R)-3-benzyloxytetradecanoic acid

Benzoic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-((2R,3R,4R,5S,6R)-5-acetoxy-6-acetoxymethyl-3-amino-4-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-6-allyloxy-5-amino-tetrahydro-pyran-4-yl ester

(R)-3-hydroxytetradecanoic acid

benzyl bromide

Downstream raw materials:

(R)-3-Benzyloxy-tetradecanoic acid {(2R,3R,4R,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy]-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-amide

(R)-3-Benzyloxy-tetradecanoic acid {(4aR,6R,7R,8R,8aS)-6-[(2R,3S,4R,5R,6R)-6-allyloxy-5-((R)-3-benzyloxy-tetradecanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-ylmethoxy]-8-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-amide