Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester
• CAS No.: 171503-78-9
• Molecular Formula: C₂₇H₄₂O₉S
• Molecular Weight: 542.691
• Mol file: 171503-78-9.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-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: 18.0%

Dicyclohexyl-methanethiol + β-D-glucose pentaacetate (604-69-3) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester (171503-78-9) + Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester (171503-67-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/jo971233k

Reference yield: 100.0%

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester (171503-78-9) → (2R,3R,4S,5S,6R)-2-Dicyclohexylmethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (197164-63-9)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; for 3h;

DOI:10.1021/jo971233k

Reference yield:

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester (171503-78-9) → (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-3-ol (197165-05-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / NaOMe / CH₂Cl₂; methanol / 3 h

2: 100 percent / camphorsulfonic acid / dimethylformamide / 3 h / 57 °C / 20 Torr

3: 93 percent / NaH / dimethylformamide / 2.5 h / Ambient temperature

4: 85 percent / triethylsilane, TFA / CH₂Cl₂ / 0.25 h

With triethylsilane; camphor-10-sulfonic acid; sodium methylate; sodium hydride; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971233k

upstream raw materials:

β-D-glucose pentaacetate

Downstream raw materials:

(2R,3R,4S,5S,6R)-2-Dicyclohexylmethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

ethyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside