(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

Base Information

• Chemical Name: (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
• CAS No.: 170708-55-1
• Molecular Formula: C₃₀H₅₄O₆S₂Si
• Molecular Weight: 602.973
• Mol file: 170708-55-1.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 25 articles about (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 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:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (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 (170708-55-1)

Guidance literature:

Multi-step reaction with 13 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.

11: Amberlite IR 120 / methanol / 4.5 h / 50 °C

12: CH₂Cl₂ / 0.5 h / Ambient temperature

13: 1.) N,N-diisopropylethylamine, 2.) K₂CO₃ / 1.) dichloromethane, 0 deg C, 1.5 h, 2.) methanol, 50 deg C, 2.5 h.

With N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; oxalyl dichloride; trifluorormethanesulfonic acid; Amberlite IR 120; potassium tert-butylate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 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-(t-butyldimethylsiloxy)-1,2-dihydroxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane (170708-55-1)

Guidance literature:

Multi-step reaction with 7 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.

5: Amberlite IR 120 / methanol / 4.5 h / 50 °C

6: CH₂Cl₂ / 0.5 h / Ambient temperature

7: 1.) N,N-diisopropylethylamine, 2.) K₂CO₃ / 1.) dichloromethane, 0 deg C, 1.5 h, 2.) methanol, 50 deg C, 2.5 h.

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; Amberlite IR 120; boron trifluoride diethyl etherate; 10-camphorsufonic acid; tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

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

Reference yield:

ethyl (R)-2-hydroxy-3-methylbutyrate (129025-85-0) → (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 (170708-55-1)

Guidance literature:

Multi-step reaction with 13 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.

11: Amberlite IR 120 / methanol / 4.5 h / 50 °C

12: CH₂Cl₂ / 0.5 h / Ambient temperature

13: 1.) N,N-diisopropylethylamine, 2.) K₂CO₃ / 1.) dichloromethane, 0 deg C, 1.5 h, 2.) methanol, 50 deg C, 2.5 h.

With N,N,N,N,N,N-hexamethylphosphoric triamide; osmium(VIII) oxide; oxalyl dichloride; trifluorormethanesulfonic acid; Amberlite IR 120; potassium tert-butylate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

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

upstream raw materials:

tert-butyldimethylsilyl trifluoroacetate

(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

t-butyldimethylsiyl triflate

(R)-4-((S)-1-{2-[(2R,3S,4R)-2-Hydroxy-3-methoxy-4-(4-methoxy-benzyloxy)-5-methyl-hexyl]-[1,3]dithian-2-yl}-ethyl)-[1,3]dioxolan-2-one

Downstream raw materials:

(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