[(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester
• CAS No.: 81366-49-6
• Molecular Formula: C₂₃H₃₉NO₆Si₂
• Molecular Weight: 481.737
• Mol file: 81366-49-6.mol

Synonyms:

Chemical Property of [(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester

There total 9 articles about [(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl 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:

isopropyldimethylsilyl chloride (3634-56-8) + (3R,4S,5R)-(4-hydroxy-5-hydroxymethyl-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester (81366-48-5) → [(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester (81366-49-6)

Guidance literature:

With dmap; triethylamine;

DOI:10.1246/cl.1982.1271

Reference yield:

(2R,3S)-2-Benzyloxycarbonylamino-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propionic acid tert-butyl ester (81366-41-8) → [(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester (81366-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid, water / 7 h / 0 °C

2: triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 1 h / 0 °C

With dmap; water; triethylamine; trifluoroacetic acid; In N,N-dimethyl-formamide;

DOI:10.1246/cl.1982.145

Reference yield:

3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-[(R)-2-hydroxy-1-methyl-2-phenyl-prop-(E)-ylideneamino]-propionic acid tert-butyl ester → [(3R,4S,5R)-4-(Isopropyl-dimethyl-silanyloxy)-5-(isopropyl-dimethyl-silanyloxymethyl)-2-oxo-tetrahydro-furan-3-yl]-carbamic acid benzyl ester (81366-49-6)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / -128 deg C -> room temperature

3: trifluoroacetic acid, water / 7 h / 0 °C

4: triethylamine, 4-(dimethylamino)pyridine / dimethylformamide / 1 h / 0 °C

With dmap; water; triethylamine; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1246/cl.1982.145

upstream raw materials:

isopropyldimethylsilyl chloride

(3R,4S,5R)-(4-hydroxy-5-hydroxymethyl-2-oxotetrahydrofuran-3-yl)carbamic acid benzyl ester

(2R,3S)-2-Benzyloxycarbonylamino-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propionic acid tert-butyl ester

(2S,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-oxirane-2-carboxylic acid ethyl ester