((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 669015-54-7
• Molecular Formula: C₂₁H₃₄O₅Si
• Molecular Weight: 394.583
• Mol file: 669015-54-7.mol

Synonyms:((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane

There total 4 articles about ((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane 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: 90.0%

5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (2592-42-9,23202-83-7) + t-butyldimethylsiyl triflate (69739-34-0) → ((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane (669015-54-7)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetlet.2003.11.001

Reference yield:

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (23202-83-7,2592-42-9) → ((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane (669015-54-7)

Guidance literature:

Multi-step reaction with 3 steps

1: (COCl)2; DMSO; TEA

2: NaBH₄ / methanol / 0 °C

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; TEA; dimethyl sulfoxide; In methanol; dichloromethane; 1: Swern oxidation;

DOI:10.1016/j.tetlet.2003.11.001

Reference yield:

benzyl bromide (100-39-0) → ((3aR,5R,6R,6aR)-5-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-tert-butyl-dimethyl-silane (669015-54-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / (Bu₃Sn)2O; TBAB / toluene / 72 h / 90 °C

2: (COCl)2; DMSO; TEA

3: NaBH₄ / methanol / 0 °C

4: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; oxalyl dichloride; TEA; tetrabutylammomium bromide; dimethyl sulfoxide; bis(tri-n-butyltin)oxide; In methanol; dichloromethane; toluene; 2: Swern oxidation;

DOI:10.1016/j.tetlet.2003.11.001

upstream raw materials:

5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

t-butyldimethylsiyl triflate

5-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

benzyl bromide

Downstream raw materials:

1,2-O-isopropylidene-3-C-methyl-O-benzyl-5,6-deoxy-6-dibenzylphosphono-α-D-allofuranose

(3R,4R)-dibenzyl-3-formyloxy-4-methyl-O-benzyl-5-oxopentylphosphonate

[2-((3aR,5R,6R,6aR)-6-Hydroxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-phosphonic acid dibenzyl ester

[2-((3aR,5R,6R,6aR)-6-Hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-phosphonic acid dibenzyl ester