Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester

Base Information

• Chemical Name: Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester
• CAS No.: 622832-75-1
• Molecular Formula: C₂₉H₃₀O₅
• Molecular Weight: 458.554
• Mol file: 622832-75-1.mol

Synonyms:Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester

Chemical Property of Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester

There total 13 articles about Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl 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:

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) → Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester (622832-75-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: NaH / dimethylformamide / 2 h / 20 °C

1.2: 88 percent / dimethylformamide / 12 h / 20 °C

2.1: BH₃*Me₂S / CH₂Cl₂ / 3 h / 20 °C

2.2: 68 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 90 percent / Ph₃P; CBr₄ / CH₂Cl₂ / 2 h / 20 °C

4.1: Zn / aq. ethanol / 0.5 h / 90 °C

5.1: 59 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran / 12 h / 20 °C

6.1: Me₃SiCl; DMAP; Et₃N / acetonitrile / 12 h / 20 °C

6.2: 54 percent / p-TsOH / acetonitrile / 3 h / 20 °C

7.1: 95 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

8.1: 20 mg / Mo(CO)6 / acetonitrile; H₂O / 1.5 h / 90 °C

9.1: DIBALH / toluene / 0.5 h / -78 °C

9.2: 10 mg / TBAF / tetrahydrofuran / 4 h / 20 °C

10.1: 1 h / 130 °C

10.2: 26 mg / Ac₂O / 96 h / 140 °C

With dmap; chloro-trimethyl-silane; hexacarbonyl molybdenum; carbon tetrabromide; dimethylsulfide borane complex; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; zinc; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 5.1: Henry reaction;

DOI:10.1021/ol035424n

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester (622832-75-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 90 percent / Ph₃P; CBr₄ / CH₂Cl₂ / 2 h / 20 °C

2.1: Zn / aq. ethanol / 0.5 h / 90 °C

3.1: 59 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran / 12 h / 20 °C

4.1: Me₃SiCl; DMAP; Et₃N / acetonitrile / 12 h / 20 °C

4.2: 54 percent / p-TsOH / acetonitrile / 3 h / 20 °C

5.1: 95 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

6.1: 20 mg / Mo(CO)6 / acetonitrile; H₂O / 1.5 h / 90 °C

7.1: DIBALH / toluene / 0.5 h / -78 °C

7.2: 10 mg / TBAF / tetrahydrofuran / 4 h / 20 °C

8.1: 1 h / 130 °C

8.2: 26 mg / Ac₂O / 96 h / 140 °C

With dmap; chloro-trimethyl-silane; hexacarbonyl molybdenum; carbon tetrabromide; diisobutylaluminium hydride; triethylamine; triphenylphosphine; zinc; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; acetonitrile; 3.1: Henry reaction;

DOI:10.1021/ol035424n

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (7177-79-9,13035-24-0,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9,13225-19-9) → Formic acid (1R,4S,5R,6R)-4,5,6-tris-benzyloxy-cyclohex-2-enylmethyl ester (622832-75-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: BH₃*Me₂S / CH₂Cl₂ / 3 h / 20 °C

1.2: 68 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 90 percent / Ph₃P; CBr₄ / CH₂Cl₂ / 2 h / 20 °C

3.1: Zn / aq. ethanol / 0.5 h / 90 °C

4.1: 59 percent / 1,1,3,3-tetramethylguanidine / tetrahydrofuran / 12 h / 20 °C

5.1: Me₃SiCl; DMAP; Et₃N / acetonitrile / 12 h / 20 °C

5.2: 54 percent / p-TsOH / acetonitrile / 3 h / 20 °C

6.1: 95 percent / Et₃N / CH₂Cl₂ / 12 h / 20 °C

7.1: 20 mg / Mo(CO)6 / acetonitrile; H₂O / 1.5 h / 90 °C

8.1: DIBALH / toluene / 0.5 h / -78 °C

8.2: 10 mg / TBAF / tetrahydrofuran / 4 h / 20 °C

9.1: 1 h / 130 °C

9.2: 26 mg / Ac₂O / 96 h / 140 °C

With dmap; chloro-trimethyl-silane; hexacarbonyl molybdenum; carbon tetrabromide; dimethylsulfide borane complex; diisobutylaluminium hydride; triethylamine; triphenylphosphine; zinc; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; acetonitrile; 4.1: Henry reaction;

DOI:10.1021/ol035424n

upstream raw materials:

orthoformic acid triethyl ester

(1S,2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-(hydroxymethyl)cyclohexane-1,2-diol

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

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

Downstream raw materials:

((1R,2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-7-oxabicyclo-[4.1.0]heptan-2-yl)methanol (+)-2,3,4-tri-O-benzylcyclophellitol

(1R,2R,5S,6S)-5,6-bis(benzyloxy)-2-{[(tert-butyldimethylsilyl)-oxy]methyl}cyclohex-3-en-1-ol