(2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran

Base Information

• Chemical Name: (2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran
• CAS No.: 1442018-16-7
• Molecular Formula: C₃₈H₄₂O₆S
• Molecular Weight: 626.814
• Mol file: 1442018-16-7.mol

Synonyms:(2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran

Chemical Property of (2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran

There total 4 articles about (2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]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: 80.0%

(2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tert-butyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran (1426171-73-4) → (2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran (1442018-16-7)

Guidance literature:

With aluminum oxide; potassium peroxomonosulfate; water; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1111/cbdd.13408

Reference yield:

1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-2-C-(4-tert-butylphenyl)thiomethyl-D-glucopyranose → (2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran (1442018-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere; Molecular sieve

2: aluminum oxide; water; Oxone / dichloromethane / 12 h / 20 °C

With aluminum oxide; Oxone; boron trifluoride diethyl etherate; water; In dichloromethane; 1: |Friedel-Crafts Alkylation;

DOI:10.1016/j.ejmech.2014.09.060

Reference yield:

4-t-butylbenzenethiol (2396-68-1) → (2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tertbutyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran (1442018-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

1.2: 0.08 h / 20 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / 0 °C / Inert atmosphere; Molecular sieve

3.1: aluminum oxide; water; Oxone / dichloromethane / 12 h / 20 °C

With aluminum oxide; Oxone; boron trifluoride diethyl etherate; water; sodium hydride; In dichloromethane; N,N-dimethyl-formamide; mineral oil; 2.1: |Friedel-Crafts Alkylation;

DOI:10.1016/j.ejmech.2014.09.060

upstream raw materials:

(2R,3S,4R,4aS,10bS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tert-butyl-2,3,4,4a,5,10b-hexahydrothiochromeno[4,3-b]pyran

4-t-butylbenzenethiol

C₃₀H₃₃IO₆

Downstream raw materials:

(2R,3S,4R,4aS,10bR)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-9-tert-butyl-2,3,4,4a,5,10b-hexahydro-S,S-dioxothiochromeno[4,3-b]pyran