Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester

Base Information

• Chemical Name: Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester
• CAS No.: 89726-66-9
• Molecular Formula: C₂₂H₂₄O₆S
• Molecular Weight: 416.495
• Mol file: 89726-66-9.mol

Synonyms:

Chemical Property of Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester

There total 5 articles about Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl 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:

L-arabinofuranose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2,36562-42-2) → Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester (89726-66-9,89726-79-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / p-TsOH / 48 h / 60 °C

2: 90 percent / dimethoxypropane, p-TsOH / 12 h / Ambient temperature

3: 1.) MeLi / 1.) THF, ether, -78 deg C, 15 min, 2.) THF, ether, from -78 deg C to RT, 45 min

With dimethoxypropane; methyllithium; toluene-4-sulfonic acid;

DOI:10.1021/jo00222a023

Reference yield:

1-O-benzyl-L-lyxose (5329-50-0,7473-38-3,10548-61-5,18403-12-8,26685-75-6,61134-26-7,70797-93-2,84588-33-0,89726-77-2,89726-80-7) → Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester (89726-66-9,89726-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / dimethoxypropane, p-TsOH / 12 h / Ambient temperature

2: 1.) MeLi / 1.) THF, ether, -78 deg C, 15 min, 2.) THF, ether, from -78 deg C to RT, 45 min

With dimethoxypropane; methyllithium; toluene-4-sulfonic acid;

DOI:10.1021/jo00222a023

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → Thiocarbonic acid O-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl) ester O-phenyl ester (89726-66-9,89726-79-4)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid

2: p-toluenesulfonic acid / acetone / 23 °C

3: 1.) MeLi / 1.) THF, -78 deg C

With methyllithium; toluene-4-sulfonic acid; In acetone;

DOI:10.1021/jo00182a037

upstream raw materials:

1-O-benzyl-2,3-isopropylidene-L-lyxopyranose

phenylcarbonochloridothioate

L-arabinofuranose

1-O-benzyl-L-lyxose

Downstream raw materials:

(3aR,7S,7aR)-7-Allyl-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

pseudomonic acid C

Methanesulfonic acid (2S,3S)-1-[1-benzenesulfonyl-2-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyl ester

(4R,5S)-2-Benzenesulfonyl-1-((3aR,7S,7aR)-4-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hexan-3-ol