(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran
• CAS No.: 197164-71-9
• Molecular Formula: C₄₇H₅₈O₅S
• Molecular Weight: 735.041
• Mol file: 197164-71-9.mol

Synonyms:(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran

Chemical Property of (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran

There total 4 articles about (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran 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: 93.0%

benzyl bromide (100-39-0) + dicyclohexylmethyl 1-thio-β-D-glucopyranoside (197164-66-2) → (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran (197164-71-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 18h;

DOI:10.1016/0040-4039(95)01222-4

Reference yield:

Dicyclohexyl-methanethiol → (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran (197164-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 18 percent / TMSOTf / CH₂Cl₂ / 16 h / Ambient temperature

2: NaOMe / CH₂Cl₂; methanol / 3 h

3: NaH / dimethylformamide / 18 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971233k

Reference yield:

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester (171503-67-6) → (2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran (197164-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / CH₂Cl₂; methanol / 3 h

2: NaH / dimethylformamide / 18 h / Ambient temperature

With sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo971233k

upstream raw materials:

benzyl bromide

dicyclohexylmethyl 1-thio-β-D-glucopyranoside

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

β-D-glucose pentaacetate

Downstream raw materials:

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

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