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

Base Information

• Chemical Name: 1,2-O-isopropylidene-3-C-methyl-O-benzyl-5,6-deoxy-6-dibenzylphosphono-α-D-allofuranose
• CAS No.: 669015-57-0
• Molecular Formula: C₃₁H₃₇O₇P
• Molecular Weight: 552.604

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 9 articles about 1,2-O-isopropylidene-3-C-methyl-O-benzyl-5,6-deoxy-6-dibenzylphosphono-α-D-allofuranose 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: 73.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + [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 (669015-56-9) → 1,2-O-isopropylidene-3-C-methyl-O-benzyl-5,6-deoxy-6-dibenzylphosphono-α-D-allofuranose (669015-57-0)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; cyclohexane; at 20 ℃;

DOI:10.1016/j.tetlet.2003.11.001

Reference yield:

5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose (34311-63-2) → 1,2-O-isopropylidene-3-C-methyl-O-benzyl-5,6-deoxy-6-dibenzylphosphono-α-D-allofuranose (669015-57-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaBH₄ / methanol / 0 °C

2.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

3.1: 98 percent / H₂ / Pd/C / ethyl acetate / 144 h

4.1: TEA / CCl₄ / -40 °C

5.1: n-BuLi; HMPA / tetrahydrofuran / -78 °C

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: (COCl)2; DMSO; TEA

7.2: 68 percent / tetrahydrofuran

8.1: 73 percent / CF₃SO₃H / CH₂Cl₂; cyclohexane / 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; trifluorormethanesulfonic acid; TEA; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; cyclohexane; ethyl acetate; 7.1: Swern oxidation;

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) → 1,2-O-isopropylidene-3-C-methyl-O-benzyl-5,6-deoxy-6-dibenzylphosphono-α-D-allofuranose (669015-57-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (COCl)2; DMSO; TEA

2.1: NaBH₄ / methanol / 0 °C

3.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

4.1: 98 percent / H₂ / Pd/C / ethyl acetate / 144 h

5.1: TEA / CCl₄ / -40 °C

6.1: n-BuLi; HMPA / tetrahydrofuran / -78 °C

7.1: TBAF / tetrahydrofuran / 20 °C

8.1: (COCl)2; DMSO; TEA

8.2: 68 percent / tetrahydrofuran

9.1: 73 percent / CF₃SO₃H / CH₂Cl₂; cyclohexane / 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; trifluorormethanesulfonic acid; TEA; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; palladium on activated charcoal; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; cyclohexane; ethyl acetate; 1.1: Swern oxidation / 8.1: Swern oxidation;

DOI:10.1016/j.tetlet.2003.11.001

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

[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

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

5-O-benzyl-3-oxo-1,2-O-isopropylidene-α-D-xylofuranose

Downstream raw materials:

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

((3R,4S)-4-Benzyloxy-3,5-dihydroxy-4-methyl-pentyl)-phosphonic acid dibenzyl ester

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