(2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane

Base Information

• Chemical Name: (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane
• CAS No.: 170708-54-0
• Molecular Formula: C₂₇H₄₄O₆S₂
• Molecular Weight: 528.775
• Mol file: 170708-54-0.mol

Synonyms:(2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane

Chemical Property of (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane

There total 20 articles about (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane 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:

(2R,3S)-1,2-isopropylidenedioxy-4-methyl-3-(1,3-dithian-2-yl)-butane (170708-53-9) + (2R,3R,4R)-1,2-epoxy-3-methoxy-4-(4-methoxybenzyl)oxy-5-methylhexane (170708-52-8) → (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane (170708-54-0)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium; In tetrahydrofuran; at -20 ℃; for 2h; Yield given;

DOI:10.1016/0040-4039(95)01436-L

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane (170708-54-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 63 percent / CF₃SO₃H / diethyl ether / 0.5 h / 0 °C

2: 92 percent / diisobutylaluminum hydride / CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) to 0 deg C, 2 h.

3: DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) to 0 deg C, 1 h.

4: 1.) NaH / 1.) THF, room temperature, 30 min, 2.) THF, -78 deg C, 15 min, and room temperature, 1.5 h.

5: 96 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / 1.) -78 deg C, 20 min, 2.) to 0 deg C, 2 h.

6: 62 percent / 4-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 48 h / -20 °C

7: Et₃N / CH₂Cl₂ / 0 °C

8: t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 1.) -78 deg C, 15 min, 2.) 0 deg C, 30 min.

9: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1.5 h.

10: 1.) t-BuLi, HMPA / 1.) THF, pentane, -20 deg C, 2 h, 2.) THF, -20 deg C, 1 h.

With N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; oxalyl dichloride; trifluorormethanesulfonic acid; potassium tert-butylate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4020(97)00228-7

Reference yield:

(2R,3R)-3-methyl-butan-1,2,4-triol (74213-65-3) → (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane (170708-54-0)

Guidance literature:

Multi-step reaction with 4 steps

1: TsOH*H₂O / 48 h / Ambient temperature

2: oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 1.) -78 deg C, 30 min, 2.) to 0 deg C, 1 h.

3: 1.) BF₃*Et₂O, 2.) (dl)-camphorsulfonic acid / 1.) dichloromethane, room temperature, 2 h, 2.) room temperature, overnight.

4: 1.) t-BuLi, HMPA / 1.) THF, pentane, -20 deg C, 2 h, 2.) THF, -20 deg C, 1 h.

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; boron trifluoride diethyl etherate; 10-camphorsufonic acid; tert.-butyl lithium; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(97)00228-7

upstream raw materials:

(2R,3S)-1,2-isopropylidenedioxy-4-methyl-3-(1,3-dithian-2-yl)-butane

(2R,3R,4R)-1,2-epoxy-3-methoxy-4-(4-methoxybenzyl)oxy-5-methylhexane

O-(4-methoxybenzyl)-trichloroacetimidate

(2R,3R)-3-methyl-butan-1,2,4-triol

Downstream raw materials:

(2R,3S,6R,7S,8R)-6-(t-butyldimethylsiloxy)-1,2-dihydroxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane

tautomycin

(2R,3S,6R,7S,8R)-6-(t-butyldimethylsiloxy)-1,2-epoxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane

(4R,5S,6R)-4-Isopropyl-5-methoxy-2-(4-methoxy-phenyl)-6-[2-((S)-(R)-1-oxiranyl-ethyl)-[1,3]dithian-2-ylmethyl]-[1,3]dioxane