2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester
CAS No.:440339-69-5
Molecular Formula:C₂₈H₃₅IO₅
Molecular Weight:578.487
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

Suppliers and Price of 2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

There total 7 articles about 2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl 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: 85.0%

: 440339-68-4
2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester

: 1730-25-2
allylmagnesium bromide

: 440339-69-5
2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: 2,2-Dimethyl-propionic acid (2S,3S,4S,5R)-4,5-bis-benzyloxy-2-iodomethyl-6-oxo-tetrahydro-pyran-3-yl ester; allylmagnesium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -10 - 0 ℃; for 0.5h;
DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

: 76491-08-2
methyl 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranoside

: 440339-69-5
2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 117 g / Amberlyst-15E / methanol / 18 h / 20 °C

2.1: 85 percent / imidazole; PPh₃; I₂ / toluene / 2 h / 20 °C

3.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

4.1: Ac₂O; aq. H₂SO₄ / 0.25 h / -5 - 0 °C

4.2: aq. HCl / tetrahydrofuran / 168 h / 20 °C

4.3: 61.0 g / Ac₂O / dimethylsulfoxide / 12 h / 20 °C

5.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

5.2: 85 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0.5 h / -10 - 0 °C

With 1H-imidazole; dmap; Amberlyst-15E; sulfuric acid; iodine; acetic anhydride; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(02)00044-3

Reference yield:

: 87326-88-3
methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside

: 440339-69-5
2,2-Dimethyl-propionic acid (2S,3S,4R,5S,6S)-6-allyl-4,5-bis-benzyloxy-2-iodomethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: DMAP / CH₂Cl₂ / 48 h / 20 °C

2.1: Ac₂O; aq. H₂SO₄ / 0.25 h / -5 - 0 °C

2.2: aq. HCl / tetrahydrofuran / 168 h / 20 °C

2.3: 61.0 g / Ac₂O / dimethylsulfoxide / 12 h / 20 °C

3.1: tetrahydrofuran; diethyl ether / 1 h / -78 °C

3.2: 85 percent / Et₃SiH; BF₃*OEt₂ / acetonitrile / 0.5 h / -10 - 0 °C

With dmap; sulfuric acid; acetic anhydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/S0040-4020(02)00044-3