(3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane
• CAS No.: 952716-09-5
• Molecular Formula: C₂₅H₄₀O₆Si
• Molecular Weight: 464.674
• Mol file: 952716-09-5.mol

Synonyms:(3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

Chemical Property of (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

There total 3 articles about (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-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: 83.0%

(3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol (952716-08-4) + allyl bromide (106-95-6) → (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane (952716-09-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 4.5h; Heating;

DOI:10.1021/jo070846m

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0) → (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane (952716-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / imidazole / dimethylformamide / cooling

2: 83 percent / NaH / tetrahydrofuran / 4.5 h / Heating

With 1H-imidazole; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo070846m

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (3aR,4aR,5R,6R)-5-allyloxymethyl-6-benzyloxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane (952716-09-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / imidazole / dimethylformamide / cooling

2: 83 percent / NaH / tetrahydrofuran / 4.5 h / Heating

With 1H-imidazole; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo070846m

upstream raw materials:

(3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

allyl bromide

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3aR,4aR,5R,6R)-(5-allyloxymethyl-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol

(2'S,3'R,4'R,5'R,4aS,5aR)-4'-acetoxy-3'-benzyloxy-6-benzyl-5'-(1H,3H-pyrimidyl-2,4-dion-1-yl)-6-aza-3,5-dioxa-bicyclo[4.2.1]nonanespiro[1.2']tetrahydro-furan

(2'S,3'R,3'aR,6'aR,4aR,6aS)-6-benzyl-3'-benzyloxy-6-aza-3,5-dioxabicyclo[4.2.1]nonane-spiro-[1.2]-1',4',6'-trioxo-bicyclo[3.3.0]octane