(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran

Base Information

• Chemical Name: (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran
• CAS No.: 194800-88-9
• Molecular Formula: C₂₈H₂₉IO₅
• Molecular Weight: 572.44
• Mol file: 194800-88-9.mol

Synonyms:(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran

Chemical Property of (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran

There total 1 articles about (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran 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: 79.0%

2-iodobenzyliodide (4622-38-2) + methyl 6-deoxy-6-iodo-2,3-bis-O-(phenylmethyl)-α-D-glucopyranoside (87326-88-3) → (2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran (194800-88-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran (194800-88-9) → Methanesulfonic acid (1R,2S,3R,4S,5S)-3,4-bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexyl ester (194801-00-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Hg(OCOCF₃)2 / acetone; H₂O / Ambient temperature

2: 86 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

3: 99 percent / LiAlH(OtBu)3 / tetrahydrofuran / Ambient temperature

4: 83 percent / Et₃N / CH₂Cl₂ / Ambient temperature

5: 99 percent / TBAF / tetrahydrofuran / Ambient temperature

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; lithium tri-t-butoxyaluminum hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(97)01325-7

Reference yield:

(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-(2-iodo-benzyloxy)-2-methoxy-6-methylene-tetrahydro-pyran (194800-88-9) → (2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexanone (194800-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Hg(OCOCF₃)2 / acetone; H₂O / Ambient temperature

2: 86 percent / 2,6-lutidine / CH₂Cl₂ / Ambient temperature

With 2,6-dimethylpyridine; mercury(II) trifluoroacetate; In dichloromethane; water; acetone;

DOI:10.1016/S0040-4039(97)01325-7

upstream raw materials:

2-iodobenzyliodide

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

Downstream raw materials:

(2S,3R,4S,5S)-3,4-Bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexanone

(4R,5S,6R)-5,6-Bis-benzyloxy-4-(2-iodo-benzyloxy)-cyclohex-2-enone

(1R,2R,3S,4R,5S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-benzyloxy)-cyclohexanol

Methanesulfonic acid (1R,2S,3R,4S,5S)-3,4-bis-benzyloxy-5-hydroxy-2-(2-iodo-benzyloxy)-cyclohexyl ester