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

Base Information

• Chemical Name: (3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol
• CAS No.: 952716-08-4
• Molecular Formula: C₂₂H₃₆O₆Si
• Molecular Weight: 424.61
• Mol file: 952716-08-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3aR,4aR,5R,6R)-[6-benzyloxy-5-(tert-butyldimethylsilanyloxymethyl)-2,2-dimethyltetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol 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: 60.0%

1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose (72261-44-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; cooling;

DOI:10.1021/jo070846m

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:

(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) → C23H27NO6

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / NaH / tetrahydrofuran / 4.5 h / Heating

2: 75 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

3: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -60 - 20 °C

4: 600 mg / ethanol / 26 h

5: sulfuric acid / acetonitrile; H₂O / 12 h / 20 °C

With oxalyl dichloride; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile; 3: Swern oxidation;

DOI:10.1021/jo070846m

upstream raw materials:

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-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-ylmethoxy-tert-butyl-dimethyl-silane

(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,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

(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